Papers - SAITO, Susumu

Artificial photosynthesis directed toward organic synthesis Invited Reviewed

Shogo Mori, Riku Hashimoto, Takashi Hisatomi, Kazunari Domen, Susumu Saito

Nature Communications     2025.2

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1038/s41467-025-56374-z

Selective electroreduction of CO₂ to formate by a heterogenized Ir complex using H₂O as an electron/hydrogen source Invited Reviewed

Jieun Jung, Keun Woo Lee, Naonari Sakamoto, Selvam Kaliyamoorthy, Taku Wakabayashi, Kenji Kamada, Keita Sekizawa, Shunsuke Sato, Tomiko M Suzuki, Takeshi Morikawa, Susumu Saito

EES Catalysis   Vol. 3   page： 254 - 258   2025

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

A newly synthesized tetradentate PNNP-coordinated iridium (Ir) complex, Mes IrPPh2, immobilized on a carbon material, was found to be a superior catalyst for CO₂ electrochemical reduction reaction (CO₂ERR) to give...

DOI： 10.1039/d4ey00261j

(PNCP)Ir vs (PNNP)Ir: Neutral Iridium Complex for Direct Hydrogenation of Carboxylic Acids Invited Reviewed

Koichiro Nishimoto, Naoki Noto, Yohei Kametani, Bendik Gro̷mer, Chihaya Murata, Hiroko Okuwa, Yoshihito Shiota, Kazunari Yoshizawa, Susumu Saito

Organometallics   Vol. 43 ( 23 ) page： 3013 - 3021   2024.10

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.organomet.4c00355

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Ferrocenyl PNNP Ligands-Controlled Chromium Complex-Catalyzed Photocatalytic Reduction of CO2 to Formic Acid Invited Reviewed

Taku Wakabayashi, Yohei Kametani, Eimi Tanahashi, Yoshihito Shiota, Kazunari Yoshizawa, Jieun Jung, Susumu Saito

Journal of the American Chemical Society   Vol. 146 ( 38 ) page： 25963 - 25975   2024.9

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jacs.4c03683

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PubMed

Photocatalytic CO2 Reduction Using an Osmium Complex as a Panchromatic Self-Photosensitized Catalyst: Utilization of Blue, Green and Red light Reviewed

Kenji Kamada, Jieun Jung, Chihiro Yamada, Taku Wakabayashi, Keita Sekizawa, Shunsuke Sato, Takeshi Morikawa, Shunichi Fukuzumi, Susumu Saito

Angew. Chem. Int. Ed.   Vol. 63   page： e202403866 - e202403866   2024.3

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/anie.202403886

Machine Learning Classification for Predicting Catalytic Activity of Organic Photosensitizers in Nickel(II) Salt-Promoted Phenol Synthesis Reviewed

Naoki Noto, Akira Yada, Takeshi Yanai, Susumu Saito

Angew. Chem. Int. Ed.   Vol. 62   page： e202219107   2023.1

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DOI： 10.1002/anie.202219107

Selective reduction of carboxylic acids to alcohols in the presence of alcohols by a dual bulky transition metal complex/Lewis acid catalyst Reviewed

Bendik Grømer, Shota Yoshioka, Susumu Saito*

ACS Catal.   Vol. 12   page： 1957 - 1964   2022.1

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DOI： 10.1021/acscatal.1c04392

Reaction of H2 with mitochondria-relevant metabolites using a multifunctional molecular catalyst Reviewed

Shota Yoshioka, Sota Nimura, Masayuki Naruto, Susumu Saito

Science Advances   Vol. 6 ( 43 ) page： eabc0274 - eabc0274   2020.10

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Association for the Advancement of Science (AAAS)  

The Krebs cycle is the fuel/energy source for cellular activity and therefore of paramount importance for oxygen-based life. The cycle occurs in the mitochondrial matrix, where it produces and transfers electrons to generate energy-rich NADH and FADH₂, as well as C₄-, C₅-, and C₆-polycarboxylic acids as energy-poor metabolites. These metabolites are biorenewable resources that represent potential sustainable carbon feedstocks, provided that carbon-hydrogen bonds are restored to these molecules. In the present study, these polycarboxylic acids and other mitochondria-relevant metabolites underwent dehydration (alcohol-to-olefin and/or dehydrative cyclization) and reduction (hydrogenation and hydrogenolysis) to diols or triols upon reaction with H₂, catalyzed by sterically confined iridium–bipyridyl complexes. The investigation of these single–metal site catalysts provides valuable molecular insights into the development of molecular technologies for the reduction and dehydration of highly functionalized carbon resources.

DOI： 10.1126/sciadv.abc0274

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Photocatalytic CO2 Reduction Using a Robust Multifunctional Iridium Complex toward the Selective Formation of Formic Acid Invited Reviewed

Kenji Kamada, Jieun Jung, Taku Wakabayashi, Keita Sekizawa, Shunsuke Sato, Takeshi Morikawa, Shunichi Fukuzumi, Susumu Saito

Journal of the American Chemical Society   Vol. 142 ( 23 ) page： 10261 - 10266   2020.6

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jacs.0c03097

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PubMed

Catalytic hydrogenation of carboxylic acids using low-valent and high-valent metal complexes Invited Reviewed

Yoshioka, S; Saito, S

CHEMICAL COMMUNICATIONS   Vol. 54 ( 95 )   2018.12

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DOI： 10.1039/c8cc06543h

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Diboron-Catalyzed Dehydrative Amidation of Aromatic Carboxylic Acids with Amines Invited Reviewed

Sawant Dinesh N, Bagal Dattatraya B, Ogawa Saeko, Selvam Kaliyamoorthy, Saito Susumu

ORGANIC LETTERS   Vol. 20 ( 15 ) page： 4397 - 4400   2018.8

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DOI： 10.1021/acs.orglett.8b01480

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N-Alkylation of functionalized amines with alcohols using a copper-gold mixed photocatalytic system Invited Reviewed

Lyu-Ming Wang, Yuna Morioka, Kellie Jenkinson, Andrew E. H. Wheatley, Susumu Saito, Hiroshi Naka

Scientific Reports   Vol. 8 ( 1 )   2018.5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Nature Publishing Group  

Direct functionalization of amino groups in complex organic molecules is one of the most important key technologies in modern organic synthesis, especially in the synthesis of bio-Active chemicals and pharmaceuticals. Whereas numerous chemical reactions of amines have been developed to date, a selective, practical method for functionalizing complex amines is still highly demanded. Here we report the first late-stage N-Alkylation of pharmaceutically relevant amines with alcohols at ambient temperature. This reaction was achieved by devising a mixed heterogeneous photocatalyst in situ prepared from Cu/TiO2 and Au/TiO2. The mixed photocatalytic system enabled the rapid N-Alkylation of pharmaceutically relevant molecules, the selective mono-and di-Alkylation of primary amines, and the non-symmetrical dialkylation of primary amines to hetero-substituted tertiary amines.

DOI： 10.1038/s41598-018-25293-z

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PubMed

Photocatalytic hydrogenolysis of allylic alcohols for rapid access to platform chemicals and fine chemicals Invited Reviewed

Yuki Takada, Joaquim Caner, Hiroshi Naka, Susumu Saito

Pure and Applied Chemistry   Vol. 90 ( 1 ) page： 167 - 174   2018.1

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Walter de Gruyter GmbH  

A brief account of our recent work on the chemo-, regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to alkenes promoted by palladium-loaded titanium oxide (Pd/TiO2) photocatalysts is presented. Since methanol is employed as the reducing agent, the method does not involve stoichiometric generation of salt waste. The photocatalytic hydrogenolysis proceeds at room temperature, and is compatible with the presence of functional groups such as C=C double bonds and hydroxyl groups at non-allylic positions. The regioselectivity is predictable: the hydrogen atom is predominantly incorporated into the sterically less hindered carbon atom of the allylic moiety. This protocol should provide straightforward green access to a range of platform chemicals (exemplified by the two-step synthesis of propylene from glycerol) and fine chemicals [e.g. (S)-(+)-lavandulol from (R)-(-)-carvone] without the need for protection/deprotection steps.

DOI： 10.1515/pac-2017-0501

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Scopus

Catalytic transformation of functionalized carboxylic acids using multifunctional rhenium complexes Invited Reviewed

Masayuki Naruto, Santosh Agrawal, Katsuaki Toda, Susumu Saito

SCIENTIFIC REPORTS   Vol. 7   2017.6

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：NATURE PUBLISHING GROUP  

Carboxylic acids (CAs) are one of the most ubiquitous and important chemical feedstocks available from biorenewable resources, CO2, and the petrochemical industry. Unfortunately, chemoselective catalytic transformations of CHnCO2H (n = 1-3) groups into other functionalities remain a significant challenge. Herein, we report rhenium(V) complexes as extremely effective precatalysts for this purpose. Compared to previously reported heterogeneous and homogeneous catalysts derived from high- or low-valent metals, the present method involves a alpha-C-H bond functionalization, a hydrogenation, and a hydrogenolysis, which affords functionalized alcohols with a wide substrate scope and high chemoselectivity under relatively mild reaction conditions. The results represent an important step toward a paradigm shift from 'low-valent' to 'high-valent' metal complexes by exploring a new portfolio of selective functional group transformations of highly oxygenated organic substrates, as well as toward the exploitation of CAs as a valuable biorenewable feedstock.

DOI： 10.1038/s41598-017-03436-y

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PubMed

Multifaceted catalytic hydrogenation of amides via diverse activation of a sterically confined bipyridine-ruthenium framework Invited Reviewed

Takashi Miura, Masayuki Naruto, Katsuaki Toda, Taiki Shimomura, Susumu Saito

SCIENTIFIC REPORTS   Vol. 7   2017.5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：NATURE PUBLISHING GROUP  

Amides are ubiquitous and abundant in nature and our society, but are very stable and reluctant to salt-free, catalytic chemical transformations. Through the activation of a "sterically confined bipyridineruthenium (Ru) framework (molecularly well-designed site to confine adsorbed H-2 in)" of a precatalyst, catalytic hydrogenation of formamides through polyamide is achieved under a wide range of reaction conditions. Both C=O bond and C-N bond cleavage of a lactam became also possible using a single precatalyst. That is, catalyst diversity is induced by activation and stepwise multiple hydrogenation of a single precatalyst when the conditions are varied. The versatile catalysts have different structures and different resting states for multifaceted amide hydrogenation, but the common structure produced upon reaction with H-2, which catalyzes hydrogenation, seems to be "H-Ru-N-H."

DOI： 10.1038/s41598-017-01645-z

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PubMed

Cationic mononuclear ruthenium carboxylates as catalyst prototypes for self-induced hydrogenation of carboxylic acids Reviewed

Masayuki Naruto, Susumu Saito

NATURE COMMUNICATIONS   Vol. 6   page： 8140   2015.8

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：NATURE PUBLISHING GROUP  

Carboxylic acids are ubiquitous in bio-renewable and petrochemical sources of carbon. Hydrogenation of carboxylic acids to yield alcohols produces water as the only byproduct, and thus represents a possible next generation, sustainable method for the production of these alternative energy carriers/platform chemicals on a large scale. Reported herein are molecular insights into cationic mononuclear ruthenium carboxylates ([Ru(OCOR)](+)) as prototypical catalysts for the hydrogenation of carboxylic acids. The substrate-derived coordinated carboxylate was found to function initially as a proton acceptor for the heterolytic cleavage of dihydrogen, and subsequently also as an acceptor for the hydride from [Ru-H](+), which was generated in the first step (self-induced catalysis). The hydrogenation proceeded selectively and at high levels of functional group tolerance, a feature that is challenging to achieve with existing heterogeneous/homogeneous catalyst systems. These fundamental insights are expected to significantly benefit the future development of metal carboxylate-catalysed hydrogenation processes of bio-renewable resources.

DOI： 10.1038/ncomms9140

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PubMed

Dehydrative synthesis of chiral oxazolidinones catalyzed by alkali metal carbonates under low pressure of CO2 Invited Reviewed

Siong Wan Foo, Yuki Takada, Yusuke Yamazaki, Susumu Saito

TETRAHEDRON LETTERS   Vol. 54 ( 35 ) page： 4717 - 4720   2013.8

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Dehydrative synthesis of oxazolidinones from amino alcohols and CO2 was achieved in the presence of alkali metal carbonates such as Cs2CO3 as catalyst. It is noteworthy that 1 atm of CO2 is enough for the reaction to proceed and no special dehydrating agent is required in this system. A mechanstic study showed that the OH of amino alcohol acts as nucleophile and the OH in the carbamic acid moiety is liberated during the cyclization process. (C) 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2013.06.100

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Catalytic hydrogenation of unactivated amides enabled by hydrogenation of catalyst precursor Invited Reviewed

Takashi Miura, Ingmar E. Held, Shunsuke Oishi, Masayuki Naruto, Susumu Saito

TETRAHEDRON LETTERS   Vol. 54 ( 21 ) page： 2674 - 2678   2013.5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

A general method for catalytic hydrogenation of unactivated amides was achieved. During the catalyst induction period, a novel structural change was observed involving full hydrogenation of the interior unsaturated bonds of the pyridines of the Ru-containing catalyst precursor. Based on this observation, the mechanism of amide hydrogenation may involve a two-step pathway, wherein the Ru catalyst having an H-Ru-N-H functionality is generated in the first step, followed by the amide carbonyl group interacting with the outer, rather than the inner, sphere of the Ru catalyst. (c) 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2013.03.047

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Aldol condensation of amides using phosphazene-based catalysis Invited Reviewed

Siong Wan Foo, Shun Oishi, Susumu Saito

TETRAHEDRON LETTERS   Vol. 53 ( 40 ) page： 5445 - 5448   2012.10

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

We have developed a new method for the direct aldol condensation of unactivated amides using 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)-based phosphorous/SO42- catalysis. The SO42- species in a reaction mixture enhances the reaction rate of the catalysis. In principle, no metal sources are required for the generation of the catalyst, and there is no requirement for the use of stoichiometric quantities of an acid or base. This catalyst system is operative under relatively acidic conditions. One major advantage of carrying out the reaction under acidic conditions is that both aldehydes and acetals are capable of undergoing carbon-carbon bond formation at the alpha-carbon of amide carbonyl groups through dehydration. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2012.07.129

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Cu-I/H-2/NaOH-Catalyzed Cross-Coupling of Two Different Alcohols for Carbon-Carbon Bond Formation: "Borrowing Hydrogen"? Invited Reviewed

Takashi Miura, Osamu Kose, Feng Li, Sun Kai, Susumu Saito

CHEMISTRY-A EUROPEAN JOURNAL   Vol. 17 ( 40 ) page： 11146 - 11151   2011.9

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/chem.201101752

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PubMed

Iron/Amino Acid Catalyzed Direct N-Alkylation of Amines with Alcohols Reviewed

Yingsheng Zhao, Siong Wan Foo, Susumu Saito

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 50 ( 13 ) page： 3006 - 3009   2011

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.201006660

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Cross-coupling reaction of alcohols for carbon-carbon bond formation using pincer-type NHC/palladium catalysts Invited Reviewed

Osamu Kose, Susumu Saito

ORGANIC & BIOMOLECULAR CHEMISTRY   Vol. 8 ( 4 ) page： 896 - 900   2010

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

A cross-coupling reaction of different alcohols was achieved using a pincer-type NHC/PdBr complex as the catalyst precursor, and the reaction, under either Ar or H(2) gas, displayed a broad substrate scope with respect to both primary and secondary alcohol components, with high alcohol product selectivity.

DOI： 10.1039/b914618k

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PubMed

RhI-catalyzed Hydration of Organonitriles Under Ambient Conditions Reviewed

Akihiro Goto, Kohei Endo, Susumu Saito

Angew. Chem. Int. Ed.   Vol. 47   page： 3607-3609   2008

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Design of acid - Base catalysis for the asymmetric direct aidol reaction Invited Reviewed

S Saito, H Yamamoto

ACCOUNTS OF CHEMICAL RESEARCH   Vol. 37 ( 8 ) page： 570 - 579   2004.8

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Proper design of acid-base catalysis has been shown to be effective for achieving high reactivity and selectivity in the asymmetric direct aldol reaction during the development of diamine-Bronsted acid types of catalyst. In this study, two principal approaches have been implemented to create a new type of catalysis and high catalytic efficiency: one is the creation of a highly viable acidic function within acid-base catalysts; the other is the creation of rather complicated but more cooperatively arranged hydrogen-bond networks that would be expected to stabilize a transition state, thereby promoting new reactivity and selectivity.

DOI： 10.1021/ar030064p

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Asymmetric direct aldol reaction assisted by water and a proline-derived tetrazole catalyst Invited Reviewed

H Torii, M Nakadai, K Ishihara, S Saito, H Yamamoto

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 43 ( 15 ) page： 1983 - 1986   2004

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.200352724

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PubMed

Chiral molecular recognition by aluminum tris(2,6-diphenylphenoxide) in an asymmetric 1,4-addition Invited Reviewed

H Ito, T Nagahara, K Ishihara, S Saito, H Yamamoto

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 43 ( 8 ) page： 994 - 997   2004

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.200352809

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PubMed

Molecular recognition of alpha,beta-unsaturated carbonyl compounds using aluminum tris(2,6-diphenylphenoxide) (ATPH): Structural and conformational analysis of ATPH complexes and application to the selective vinylogous aldol reaction Invited Reviewed

S Saito, T Nagahara, M Shiozawa, M Nakadai, H Yamamoto

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 125 ( 20 ) page： 6200 - 6210   2003.5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Various alpha,beta-unsaturated carbonyl compounds were coordinated with aluminum tris(2,6-diphenylphenoxide) (ATPH) to give the corresponding Lewis acid-base complexes in a distinctive coordination fashion (selective coordination). ATPH recognizes carbonyl substrates and subsequently orients itself as it forms a stable complex through selective coordination with the carbonyl oxygen. Selective coordination also confers a conformational preference to each carbonyl compound under the steric and electronic influence of ATPH, which enables the vinylogous aldol reaction of alpha,beta-unsaturated carbonyl compounds to give the corresponding gamma-aldol products with different regio- and stereoselectivities.

DOI： 10.1021/ja0205941

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PubMed

Asymmetric carbon-carbon coupling of phenols or anilines with aryllead triacetates Invited Reviewed

T Kano, Y Ohyabu, S Saito, H Yamamoto

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 124 ( 19 ) page： 5365 - 5373   2002.5

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The asymmetric coupling of various phenol or aniline derivatives with bulky aryllead triacetates was thoroughly investigated using optically active amines, including strychnine and brucine. We found that conformationally restricted tertiary amines, as well as lithium aryloxides and molecular sieves, are essential for accelerating the rate of phenol coupling. Consequently, the reaction can be carried out at a low temperature (-40 to -20 degreesC) and gives a high degree of diastereo- and enantioselectivity. In contrast to the effectiveness of lithiation in phenol coupling, magnesation of anilines was a critical technique for aniline coupling with aryllead triacetates. Using these coupling methods, a diverse set of di-, tri, and polyaryl compounds with axial chirality can be easily obtained, and these should be useful for the construction of a variety of aryl-aryl frameworks involved in metal ligands, natural products, and artificial helical polymers.

DOI： 10.1021/ja012287l

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Diamine-protonic acid catalysts for catalytic asymmetric aldol reaction Invited Reviewed

Saito, S; Nakadai, M; Yamamoto, H

SYNLETT   ( 8 ) page： 1245 - 1248   2001.8

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Aluminum tris(2,6-diphenylphenoxide)-ArCOCl complex for nucleophilic dearomatic functionalization Invited Reviewed

S Saito, T Sone, M Murase, H Yamamoto

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 122 ( 41 ) page： 10216 - 10217   2000.10

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/ja0014382

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Molecular recognition of carbonyl compounds using aluminum tris(2,6-diphenylphenoxide) (ATPH): New regio- and stereoselective alkylation of alpha,beta-unsaturated carbonyl compounds Invited Reviewed

S Saito, M Shiozawa, T Nagahara, M Nakadai, H Yamamoto

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 122 ( 32 ) page： 7847 - 7848   2000.8

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/ja000789d

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Asymmetric coupling of phenols with arylleads Invited Reviewed

Saito, S; Kano, T; Muto, H; Nakadai, M; Yamamoto, H

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 121 ( 38 ) page： 8943 - 8944   1999.9

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DOI： 10.1021/ja990646v

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Designer Lewis acid catalysts for selective organic synthesis Invited Reviewed

Yamamoto, H; Saito, S

PURE AND APPLIED CHEMISTRY   Vol. 71 ( 2 ) page： 239 - 245   1999.2

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1351/pac199971020239

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Designer Lewis acids for selective organic synthesis Invited Reviewed

Yamamoto, H; Yanagisawa, A; Ishihara, K; Saito, S

PURE AND APPLIED CHEMISTRY   Vol. 70 ( 8 ) page： 1507 - 1512   1998.8

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Conceptually new directed aldol condensation using aluminum tris(2,6-diphenylphenoxide) Invited Reviewed

Saito, S; Shiozawa, M; Ito, M; Yamamoto, H

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 120 ( 4 ) page： 813 - 814   1998.2

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DOI： 10.1021/ja972765l

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Diastereoselective aldol reaction with an acetate enolate: 2,6-bis(2-isopropylphenyl)-3,5-dimethylphenol as an extremely effective chiral auxiliary Invited Reviewed

Saito, S; Hatanaka, K; Kano, T; Yamamoto, H

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 37 ( 24 ) page： 3378 - 3381   1998

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DOI： 10.1002/(SICI)1521-3773(19981231)37:24<3378::AID-ANIE3378>3.0.CO;2-L

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Designer Lewis acid catalysts - bulky aluminium reagents for selective organic synthesis Invited Reviewed

Saito, S; Yamamoto, H

CHEMICAL COMMUNICATIONS   ( 17 ) page： 1585 - 1592   1997.9

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/a607464b

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Database Construction for the Virtual Screening of the Ruthenium-Catalyzed Hydrogenation of Ketones Invited Reviewed

Haruno Nakajima, Chihaya Murata, Naoki Noto, Susumu Saito

The Journal of Organic Chemistry   Vol. 90 ( 2 ) page： 1054 - 1060   2025.1

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.joc.4c02347

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PdPt/SrTiO3:Al-catalysed redox-selective photoreduction of unsaturated carboxylic acids using minimal electron-donor and water Invited Reviewed

Shogo Mori, Farzaneh Soleymani Movahed, Sha Xue, Yuji Sakai, Daling Lu, Takashi Hisatomi, Kazunari Domen, Susumu Saito

Chemical Communications   Vol. 60 ( 93 )   2024.11

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/d4cc03791j

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Metal-Loaded Semiconductor-Photocatalysis of Alcohols for Selective Organic Synthesis: A Personal Account Invited Reviewed

Shogo Mori, Shu Sakurai, Hiroshi Naka, Susumu SAITO

Synlett   Vol. 34 ( 20 ) page： 2361 - 2373   2023.12

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/a-2124-4037

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Hydrogenation of CO2 to MeOH Catalyzed by Highly Robust (PNNP)Ir Complexes Activated by Alkali Bases in Alcohol Reviewed

Bendik Grømer, Susumu Saito*

  Vol. 62 ( 34 ) page： 14116 - 14123   2023.8

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.inorgchem.3c02412

N‐Methylation of Twenty Different α‐Amino Acid Motifs Using Methanol under Metal‐Loaded Titanium Dioxide Photocatalysis Invited Reviewed

Yuki Hashiba, Shogo Mori, Ivven Huang, Yuna Morioka, Hiroshi Naka, Susumu Saito

Asian Journal of Organic Chemistry   Vol. 12 ( 8 ) page： e202300230   2023.8

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/ajoc.202300230

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Sustainable Organic Synthesis Promoted on Titanium Dioxide using Coordinated Water and Renewable Energies/Resources Invited Reviewed

(8) Miho Yamauchi,* Hikaru Saito, Toshiki Sugimoto,* Shogo Mori, Susumu Saito*

COORDINATION CHEMISTRY REVIEWS   Vol. 472   page： 214773   2022.12

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.ccr.2022.214773

Arylamines as More Strongly Reducing Organic Photoredox Catalysts than <i>fac</i>-[Ir(ppy)₃] Invited Reviewed

Naoki Noto, Susumu Saito

ACS Catalysis   Vol. 12 ( 24 ) page： 15400 - 15415   2022.12

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Authorship：Last author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acscatal.2c05034

Web of Science

A Highly Durable, Self-Photosensitized Mononuclear Ruthenium Catalyst for CO2 Reduction Invited Reviewed

Kenji Kamada, Hiroko Okuwa, Taku Wakabayashi, Keita Sekizawa, Shunsuke Sato, Takeshi Morikawa, Jieun Jung, Susumu SAITO

Synlett   Vol. 33 ( 12 ) page： 1137 - 1141   2022.7

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

A novel mononuclear ruthenium (Ru) complex bearing a PNNP-type tetradentate ligand is introduced here as a self-photosensitized catalyst for the reduction of carbon dioxide (CO2). When the pre-activation of the Ru complex by reaction with a base was carried out, an induction period of catalyst almost disappeared and the catalyst turnover numbers (TONs) over a reaction time of 144 h reached 307 and 489 for carbon monoxide (CO) and for formic acid (HCO2H), respectively. The complex has a long lifespan as a dual photosensitizer and reduction catalyst, due to the sterically bulky and structurally robust (PNNP)Ru framework. Isotope labeling experiments under 13CO2 atmosphere indicate that CO and HCO2H were both produced from CO2.

DOI： 10.1055/a-1709-0280

Web of Science

Importance of steric bulkiness of iridium photocatalysts with PNNP tetradentate ligands for CO2 reduction Invited Reviewed

(9) Kenji Kamada, Jieun Jung,* Yohei Kametani, Taku Wakabayashi, Yoshihito Shiota, Kazunari Yoshizawa, Seong Hee Bae, Manami Muraki, Masayuki Naruto, Keita, Sekizawa, Shunsuke Sato, Takeshi Morikawa and Susumu Saito*

Chem. Commun.   Vol. 58   page： 9218 - 9221   2022.7

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DOI： 10.1039/d2cc01701f

Photocatalytic CO₂ Reduction Using an Iron–Bipyridyl Complex Supported by Two Phosphines for Improving Catalyst Durability Invited Reviewed

Taku Wakabayashi, Kenji Kamada, Keita Sekizawa, Shunsuke Sato, Takeshi Morikawa, Jieun Jung, Susumu Saito

Organometallics   Vol. 41 ( 14 ) page： 1865 - 1871   2022.5

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.organomet.2c00171

Web of Science

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of <i>N</i>-(2-Hydroxyethyl)amides into 2-Oxazolines Reviewed

Farzaneh Soleymani Movahed, Siong Wan Foo, Shogo Mori, Saeko Ogawa, Susumu Saito

The Journal of Organic Chemistry   Vol. 87 ( 1 ) page： 243 - 257   2022.1

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DOI： 10.1021/acs.joc.1c02318

Web of Science

PubMed

Recent advances in light-driven C–C bond formation via carbon dioxide activation Invited Reviewed

Synthesis   Vol. 53   page： 3263 - 3278   2021.8

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DOI： 10.1055/a-1577-5947

Preparation of platinum nanoparticle catalyst closely locating near photocatalyst titanium oxide and its catalytic activity to synthesize ethers from benzyl alcohols Reviewed

Yuki Wada, Toshiki, Akiyama, Kazuo Harada, Tetsuo Honma, Hiroshi Naka, Susumu Saito, Mitsuhiro Arisawa

RSC Adv.   Vol. 11   page： 22230 - 22237   2021.6

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DOI： 10.1039/d1ra00988e

C(sp³)–H bond functionalization with styrenes <i>via</i> hydrogen-atom transfer to an aqueous hydroxyl radical under photocatalysis Invited Reviewed

Shogo Mori, Susumu Saito

Green Chemistry   Vol. 23 ( 10 ) page： 3575 - 3580   2021.5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

<p>The redox-neutral addition of α-C–H bonds to styrenes was enabled via the hydrogen-atom transfer to aqueous hydroxyl radical generated by the oxidation of water under silver-nanoparticle-loaded titania photocatalysis.</p>

DOI： 10.1039/d1gc00753j

Web of Science

Development of Effective Bidentate Diphosphine Ligands of Ruthenium Catalysts toward Practical Hydrogenation of Carboxylic Acids Invited Reviewed

Shota Yoshioka, Ke Wen, Susumu Saito

Bulletin of the Chemical Society of Japan   Vol. 94 ( 5 ) page： 1510 - 1524   2021.5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20210023

Web of Science

Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds Between Aromatic Acids and Amines Invited Reviewed

Susumu Saito, Farzaneh Soleymani Movahed, Dinesh N. Sawant, Dattatraya B. Bagal

Synthesis   Vol. 52 ( 21 ) page： 3253 - 3262   2020.11

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using 31P NMR spectroscopy and ESI mass spectrometry.

DOI： 10.1055/s-0040-1707174

Web of Science

Development of Catalytic Reduction of Renewable Carbon Resources Using Well-Elaborated Organometallic Complexes with PNNP Tetradentate Ligands Invited Reviewed

Shota Yoshioka, Jieun Jung, Susumu Saito

Journal of Synthetic Organic Chemistry, Japan   Vol. 78 ( 9 ) page： 856 - 866   2020.9

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Society of Synthetic Organic Chemistry, Japan  

DOI： 10.5059/yukigoseikyokaishi.78.856

Catalytic Hydrogenation of N‐protected α‐Amino Acids Using Ruthenium Complexes with Monodentate Phosphine Ligands Invited Reviewed

Akari Saito, Shota Yoshioka, Masayuki Naruto, Susumu Saito

Advanced Synthesis & Catalysis   Vol. 362 ( 2 ) page： 424 - 429   2020.1

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/adsc.201901298

Web of Science

Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.201901298

Pd/TiO2-Photocatalyzed Self-Condensation of Primary Amines To Afford Secondary Amines at Ambient Temperature Reviewed

Wang Lyu-Ming, Kobayashi Kensuke, Arisawa Mitsuhiro, Saito Susumu, Naka Hiroshi

ORGANIC LETTERS   Vol. 21 ( 2 ) page： 341 - 344   2019.1

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DOI： 10.1021/acs.orglett.8b03271

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PubMed

Photocatalytic N-Methylation of Amines over Pd/TiO2 for the Functionalization of Heterocycles and Pharmaceutical Intermediates Reviewed

Wang Lyu-Ming, Jenkinson Kellie, Wheatley Andrew E. H, Kuwata Keiko, Saito Susumu, Naka Hiroshi

ACS SUSTAINABLE CHEMISTRY & ENGINEERING   Vol. 6 ( 11 ) page： 15419-15424 - 15424   2018.11

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DOI： 10.1021/acssuschemeng.8b03855

Web of Science

Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol

Yuki Takada, Joaquim Caner, Selvam Kaliyamoorthy, Hiroshi Naka, Susumu Saito

CHEMISTRY-A EUROPEAN JOURNAL   Vol. 23 ( 71 ) page： 18025 - 18032   2017.12

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(-)-carvone by avoiding otherwise necessary protection/deprotection steps.

DOI： 10.1002/chem.201704099

Web of Science

Dehydrogenation of Primary Aliphatic Alcohols by Au/TiO2 Photocatalysts Invited Reviewed

Masaki Shibata, Ryoko Nagata, Susumu Saito, Hiroshi Naka

CHEMISTRY LETTERS   Vol. 46 ( 4 ) page： 580 - 582   2017.4

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Dehydrogenation reaction of primary aliphatic alcohols to aldehydes and molecular hydrogen was achieved under UV-vis light irradiation in the presence of gold-loaded titanium dioxide (Au/TiO2) photocatalysts.

DOI： 10.1246/cl.161195

Web of Science

Investigation of the Corey Bromolactamization with N-Functionalized Allylamines Reviewed

Adrian Schulte, Simon Janich, Ernst-Ulrich Wuerthwein, Susumu Saito, Bernhard Wuensch

JOURNAL OF HETEROCYCLIC CHEMISTRY   Vol. 53 ( 6 ) page： 1827 - 1837   2016.11

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N-Allylamines were employed for the diastereoselective synthesis of 8-bromo-substituted, cis-configured perhydroquinoxalines and beta-bromoalcohols. The yield and constitution of the products depend considerably on the functionalization of the allylic N-atom. Herein the reaction of glycine-derived cyclohex-2-enamines 5 under bromolactamization conditions (LiOtBu, NBS) is reported. Methyl carbamate 5a led diastereoselectively to the cis-configured perhydroquinoxaline 6a, whereas the amides 5b and 5c provided cis, trans-configured -bromoalcohols 7b and 7c. Based on high level theoretical calculations (DFT) factors controlling the cyclization of lithiated intermediates and the relative energies of possible products are discussed.

DOI： 10.1002/jhet.2493

Web of Science

Versatile Ruthenium Complex "RuPCY" for Directed Catalytic Hydrogen Management in Organic Synthesis Invited Reviewed

Yuki Takada, Megumi Iida, Kazuki Iida, Takashi Miura, Susumu Saito

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   Vol. 74 ( 11 ) page： 1078 - 1089   2016.11

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

The ruthenium (Ru) precatalyst complex dichlorobis[2-[(dicyclohexylphosphino-kappa P)methyl]pyridine- kappa N]ruthenium(II) (RuPCY), first developed by us, was shown to be useful not only for the catalytic hydrogenation of inert carboxylic acid derivatives including amides and esters, but also for the catalytic dehydrogenation of primary (1 degrees) and secondary (2 degrees) alcohols and subsequent reactions. RuPCY is versatile, and different Ru catalysts derived therefrom are quite useful for realizing a variety of indiscrete/discrete catalytic hydrogen management (HyMA) reactions. The sequential use of different starting materials and different catalysts (all derived from RuPCY) permits otherwise challenging orthogonal HyMA processes. This accommodates, for example, a salt-free access and/or shortcut to synthetic intermediates of pharmaceutically important substances such as donepezil (Aricept (R)) and atorvastatin (Lipitor (R)).

Web of Science

Synthesis of morphan derivatives with additional substituents in 8-position Reviewed

Janine Stefaowitz, Dirk Schepmann, Constantin Daniliuc, Susumu Saito, Bernhard Wuensch

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   Vol. 71 ( 10 ) page： 1057 - 1069   2016.10

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

The morphan system (2-azabicyclo[3.3.1]no-nane) as a substructure of morphine is of major interest in medicinal chemistry. Herein, the synthesis of morphan derivatives with additional substituents at the propano bridge is reported. In order to avoid the isolation of the smelly and volatile nitrile 6 and the very polar primary amine 9, an efficient one-pot, three-step sequential transformation of the mesylate 5 into amides 10 was developed. The key step of the synthesis was the stereoselective intramolecular opening of the epoxides 11a-d leading to the exo-configured 8-hydroxymorphans 12a-d. The configuration of the exo-configured hydroxymorphan 12d bearing the kappa- and sigma-pharmacophoric 3,4-dichlorophenylacetyl moiety was inverted by oxidation and stereoselective reduction. An X-ray crystal structure analysis of the benzamide 12c confirmed the relative configuration of the hydroxymorphans 12a-d and 14d.

DOI： 10.1515/znb-2016-0129

Web of Science

Stereoselective Synthesis of cis,cis-Configured Perhydroquinoxaline-5-Carbonitrile from Cyclohex-2-en-1-ol Reviewed

Adrian Schulte, Susumu Saito, Bernhard Wuensch

JOURNAL OF HETEROCYCLIC CHEMISTRY   Vol. 53 ( 2 ) page： 533 - 536   2016.3

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cis,cis-Configured perhydroquinoxaline-5-carbonitrile 10 was synthesized stereoselectively by ditosylation of trans,cis-2,3-dihydroxycyclohexane-1-carbonitrile 4 and subsequent reaction with ethylenediamine. The diol precursor 4 was stereoselectively obtained by regioselective opening of the epoxide 3 with KCN in water avoiding hazardous Et2AlCN.

DOI： 10.1002/jhet.2322

Web of Science

N-Methylation of Amines with Methanol at Room Temperature Reviewed

Vasily N. Tsarev, Yuna Morioka, Joaquim Caner, Qing Wang, Richiro Ushimaru, Akihiko Kudo, Hiroshi Naka, Susumu Saito

ORGANIC LETTERS   Vol. 17 ( 10 ) page： 2530 - 2533   2015.5

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N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups.

DOI： 10.1021/acs.orglett.5b01063

Web of Science

PubMed

One-step synthesis of patterned polymer brushes by photocatalytic microcontact printing Invited Reviewed

Friederike Kettling, Benjamin Vonhoeren, Jennifer A. Krings, Susumu Saito, Bart Jan Ravoo

CHEMICAL COMMUNICATIONS   Vol. 51 ( 6 ) page： 1027 - 1030   2015

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

A novel method to prepare microstructured polymer brushes using TiO2 nanoparticles and photocatalytic microcontact printing is described. It is shown that ethanol amine can be polymerized to linear polyethyleneimine (PEI) driven by the photocatalytic action of TiO2. Upon UV irradiation during microcontact printing of ethanol amine with a stamp coated with TiO2 nanoparticles, patterned polymer brushes with a length of around 50 nm are obtained.

DOI： 10.1039/c4cc08646e

Web of Science

PubMed

Hydration of nitriles to amides by a chitin-supported ruthenium catalyst

Matsuoka Aki, Isogawa Takahiro, Morioka Yuna, Knappett Benjamin R, Wheatley Andrew E. H, Saito Susumu, Naka Hiroshi

RSC ADVANCES   Vol. 5 ( 16 ) page： 12152-12160   2015

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DOI： 10.1039/c4ra15682j

Bromolactamization: Key Step in the Stereoselective Synthesis of Enantiomerically Pure, cis-Configured Perhydropyrroloquinoxalines Reviewed

Adrian Schulte, Xingci Situ, Susumu Saito, Bernhard Wuensch

CHIRALITY   Vol. 26 ( 12 ) page： 793 - 800   2014.12

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Compounds based on the pyrroloquinoxaline system can interact with serotonin 5-HT3, cannabinoid CB1, and -opioid receptors. Herein, a chiral pool synthesis of diastereomerically and enantiomerically pure bromolactam (S,R,R,R)-14A is presented. Introduction of the cyclohexenyl ring at the N-atom of (S)-proline derivatives 8 or methyl (S)-pyroglutamate (12) led to the N-cyclohexenyl substituted pyrrolidine derivatives 4 and 13, respectively. All attempts to cyclize the (S)-proline derivatives 4 with a basic pyrrolidine N-atom via [3+2] cycloaddition, aziridination, or bromolactamization failed. Fast aromatization occurred during treatment of cyclohexenamines under halolactamization conditions. In contrast, reaction of a 1:1 mixture of diastereomeric pyroglutamates (S,R)-13bA and (S,S)-13bB with (LiOBu)-Bu-t and NBS provided the tricyclic bromolactam (S,R,R,R)-14A with high diastereoselectivity from (S,R)-13bA, but did not transform the diastereomer (S,S)-13bB. The different behavior of the diastereomeric pyroglutamates (S,R)-13bA and (S,S)-13bB is explained by different energetically favored conformations. Chirality 26:793-800, 2014. (c) 2014 Wiley Periodicals, Inc.

DOI： 10.1002/chir.22350

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PubMed

Stereoselective Synthesis of cis,cis-Configured Vicinal Triamines Reviewed

Adrian Sehulte, Susumu Saito, Bernhard Wuensch

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 26 ) page： 5749 - 5756   2014.9

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

The first stereoselective synthesis of a cis, cis-configured vicinal triamine was achieved, starting from N-cyclohexenylpyrrolidone (10). The reaction sequence consists of the stereoselective construction of the trans-configured 1,3-diamide 14, trans-to-cis isomerization via enols or enamines, and subsequent highly stereoselective reduction of the intermediate imine 17D to the amine 18A. The postulated reaction pathway explains the observed stereoconvergence and is supported by calculation of the heats of formation of its intermediates at the PM3 level. LiAlH4 reduction of 18A yielded the tetracyclic aminal 19, which was converted into the pyrrolidinylquinoxaline 7, which showed low to moderate affinity towards. and sigma(1) receptors.

DOI： 10.1002/ejoc.201402685

Web of Science

A Route to propylene from renewable allyl alcohol by photocatalytic transfer hydrogenolysis Reviewed

Joaquim Caner, Zijun Liu, Yuki Takada, Akihiko Kudo, Hiroshi Naka, Susumu Saito

Catal. Sci. Technol.   Vol. 4 ( 11 ) page： 4093–4098   2014

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Catalytic fluoride triggers dehydrative oxazolidinone synthesis from CO2 Invited Reviewed

Yuki Takada, Siong Wan Foo, Yusuke Yamazaki, Susumu Saito

RSC ADVANCES   Vol. 4 ( 92 ) page： 50851 - 50857   2014

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Herein, catalytic fluoride (F-) is demonstrated to be a trigger for dehydrative immobilization of atmospheric pressure CO2, such that reaction of CO2 with beta-amino alcohols derived from natural amino acids gives optically pure oxazolidinones in high yields. A synergistic combination of fluoride and organosilicon agents (e.g., Bu4NF + Ph3SiF or siloxanes) enhances the catalytic activity and functional group compatibility. This system lies at the interface between homogenous and heterogeneous catalysis, and may prove useful for the development of recoverable/reusable siloxane-based CO2 immobilization materials.

DOI： 10.1039/c4ra09609f

Web of Science

Synthesis of propylene from renewable allyl alcohol by photocatalytic transfer hydrogenolysis

Caner Joaquim, Liu Zijun, Takada Yuki, Kudo Akihiko, Naka Hiroshi, Saito Susumu

CATALYSIS SCIENCE & TECHNOLOGY   Vol. 4 ( 11 ) page： 4093-4098   2014

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DOI： 10.1039/c4cy00329b

The Dual Role of Ruthenium and Alkali Base Catalysts in Enabling a Conceptually New Shortcut to N-Unsubstituted Pyrroles through Unmasked alpha-Amino Aldehydes Reviewed

Kazuki Iida, Takashi Miura, Junki Ando, Susumu Saito

ORGANIC LETTERS   Vol. 15 ( 7 ) page： 1436 - 1439   2013.4

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

A virtually salt-free and straightforward bimolecular assembly giving N-unsubstituted pyrroles through fully unmasked a-amino aldehydes, which was enabled by the dual effects of a catalytic ruthenium complex and an alkali metal base, is reported. Either solvent-free or acceptorless dehydrogenation facilitates high atom, step, and pot economy, which are otherwise difficult to achieve in multistep operations involving protection/deprotection.

DOI： 10.1021/ol4001262

Web of Science

Reaction of an "Invisible" Frustrated N/B Lewis Pair with Dihydrogen Reviewed

Sina Schwendemann, Shunsuke Oishi, Susumu Saito, Roland Froehlich, Gerald Kehr, Gerhard Erker

CHEMISTRY-AN ASIAN JOURNAL   Vol. 8 ( 1 ) page： 212 - 217   2013.1

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

D-(+)-Camphor forms the enamine 2 with piperidine. Compound 2 adds HB(C6F5)(2) at the enamine carbon atom C3 to form a Lewis acid/Lewis base adduct (exo-/endo-isomers of 3). Exposure of 3 to dihydrogen (2.5 bar, room temperature) leads to heterolytic splitting of H-2 to form the H+/H- addition products (4, two diastereoisomers) of the "invisible" frustrated Lewis pairs (5, two diastereoisomers) that were apparently generated in situ by enamine hydroboration under equilibrium conditions.

DOI： 10.1002/asia.201200776

Web of Science

Redox-selective Generation of Aldehydes and H2 from Alcohols under Visible Light Reviewed

Zijun Liu, Joaquim Caner, Akihiko Kudo, Hiroshi Naka, *Susumu Saito

Chem. Eur. J.   Vol. 19   page： 9452–9456   2013

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Acetals of N,N-dimethylformamides: Ambiphilic behavior in converting carbon dioxide to dialkyl carbonates Reviewed

Yuki Takada, Aki Matsuoka, Ya Du, Hiroshi Naka, Susumu Saito

Chemistry Letters   Vol. 42 ( 2 ) page： 146 - 147   2013

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Carbon dioxide is immobilized into dialkyl carbonate using acetals of N,N-dimethylformamide under atmospheric pressure. No special treatment with tailor-made catalysts is needed. Use of dimethyl sulfoxide as a solvent is critical. An ambiphilic mechanism is proposed for the direct synthesis of dialkyl carbonates from acetals and carbon dioxide. © 2013 The Chemical Society of Japan.

DOI： 10.1246/cl.2013.146

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Scopus

Catalytic Hydrogenation of Unactivated Amides Using Molecular Catalyst Surface Derived from Ruthenium Complex Invited Reviewed

Takashi Miura, Ingmar E. Held, Shunsuke Oishi, Susumu Saito

Catalysts and Catalysis: Special Issue: Special Issue: Recent Trend in Catalytic Chemicals Synthesis Using Hydrogen   Vol. 54 ( 7 ) page： 455–459   2012.12

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Catalytic Hydrogenation of Unactivated Amides Using Molecular Catalyst Surface Derived from Ruthenium Complex Invited Reviewed

Takashi Miura, Ingmar E. Held, Shunsuke Oishi, Susumu Saito

Catalysts and Catalysis: Special Issue: Special Issue: Recent Trend in Catalytic Chemicals Synthesis Using Hydrogen   Vol. 54 ( 7 ) page： 455–459   2012.12

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Language：Japanese   Publishing type：Research paper (scientific journal)  

Double Molecular Recognition with Aminoorganoboron Complexes: Selective Alcoholysis of beta-Dicarbonyl Derivatives Reviewed

Shunsuke Oishi, Susumu Saito

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 51 ( 22 ) page： 5395 - 5399   2012

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.201200304

Web of Science

Selective N-Alkylation of Amines with Alcohols by Using Non-Metal-Based Acid-Base Cooperative Catalysis Reviewed

Ya Du, Shunsuke Oishi, Susumu Saito

CHEMISTRY-A EUROPEAN JOURNAL   Vol. 17 ( 44 ) page： 12262 - 12267   2011.10

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/chem.201102446

Web of Science

One-Pot Nitrile Aldolization/Hydration Operation Giving beta-Hydroxy Carboxamides Reviewed

Akihiro Goto, Hiroshi Naka, Ryoji Noyori, Susumu Saito

CHEMISTRY-AN ASIAN JOURNAL   Vol. 6 ( 7 ) page： 1740 - 1743   2011.7

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

DOI： 10.1002/asia.201000921

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PubMed

N Alkylation of Amines with Alcohols by Using Non Metal Based Acid/base Cooperative Catalysis Reviewed

Ya Du, Shunsuke Oishi, Susumu Saito

Chem. Eur. J.   Vol. 17   page： 12262–12267   2011

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Synthesis of carbonates directly from 1 atm CO2 and alcohols using CH2Cl2 Reviewed

Yusuke Yamazaki, Kasumi Kakuma, Ya Du, Susumu Saito

TETRAHEDRON   Vol. 66 ( 51 ) page： 9675 - 9680   2010.12

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

We introduced here a new one-pot, general procedure for the preparation of dialkyl carbonates from alcohols in a straightforward fashion under 1 atm pressure of CO2 using Cs2CO3 and CH2Cl2 as key reagents. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2010.10.051

Web of Science

Synthesis of a Silanol-substituted Proline Analog as Organocatalyst Reviewed

Daniel Kracht, Susumu Saito, Roland Froehlich, Bernhard Wuensch

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   Vol. 64 ( 10 ) page： 1169 - 1175   2009.10

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A proline-derived silanol, was designed as a novel potential organocatalyst, and synthesized starting from the tetrazole 3. The central idea was the combination of all acidic (tetrazole) and a basic functionality (pyrrolidine) with a silanol moiety in the same molecule. The synthesis of 7 was performed ill four reaction steps starting with the tetrazole 3. In the solid state (X-ray crystal Structure analysis) the crucial functional groups show a favorable orientation. A chiral HPLC method and a chiral capillary electrophoresis method have been established for the investigation of the kinetic resolution of the racemic alcohols 9 and 11. Acetylation reactions of alcohols were not accelerated by the organocatalyst 7, and the produced ee values were rather low.

Web of Science

Importance of Open Structure of Nonmetal Based Catalyst in Hydrogen Bond Promoted Methanolysis of Activated Amide: Structure Dynamics between Monomer and Dimer Enabling Recombinant Covalent, Dative, and Hydrogen Bonds Reviewed

Shunsuke Oishi, Junichi Yoshimoto, Susumu Saito

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 131 ( 25 ) page： 8748 - +   2009.7

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We disclosed structural dynamics hidden behind a series of aminoorganoboron (AOB) compounds that involved a recombinant of covalent, dative, and hydrogen bonds. A combination process occurred via reorganizing elements and bonds between the two major structures (open and closed), which were chemically switchable through precise adjustment of either acidic or basic conditions. The structural dynamics favoring an open structure seem to be more important for catalysis, as represented by methanolysis of activated amides.

DOI： 10.1021/ja9029494

Web of Science

Synthesis of 1,4-Diazabicyclo[3.3.1]nonan-6-ones Reviewed

Daniel Kracht, Susumu Saito, Bernhard Wuensch

AUSTRALIAN JOURNAL OF CHEMISTRY   Vol. 62 ( 12 ) page： 1684 - 1689   2009

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1,4-Diazabicyclo[3.3.1] nonanes (aza-morphans) represent conformationally constrained piperazine derivatives. Herein, we report a six-step synthesis of the benzyl and allyl substituted bicyclic ketones 3a and 3b, which represent interesting building blocks for the synthesis of conformationally restricted receptor ligands. The key steps of the synthesis are the regioselective addition of ethyl acrylate to the piperazine 8, the sodium hexamethyldisilazide-induced Dieckmann cyclization of the diesters 10, and the decarboxylation of the enol esters 11 with dilute HCl. The complete sequence is only successful when a benzyl (10a) or allyl moiety (10b) is attached to N-1, since the tosyl derivative 10f failed to give a Dieckmann cyclization product, and the decarboxylation failed with the acyl derivatives 11c and 11d.

DOI： 10.1071/CH09206

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Aqua-aminoorganoboron Catalyst: Engineering Single Water Molecule to Act as an Acid Catalyst in Nitro Aldol Reaction Invited Reviewed

Junichi Yoshimoto, Christian A. Sandoval, Susumu Saito

CHEMISTRY LETTERS   Vol. 37 ( 12 ) page： 1294 - 1295   2008.12

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We have disclosed the catalytic potential hidden behind a series of aqua-aminoorganoboron compounds in the formation and reaction of nitronate species. The pivotal role of a single-coordinated water molecule in the catalyst was demonstrated by comparison with the D2O-analogue. The present results provide a new strategy for the design of metal-free catalysts which function via elaborative hydrogen-bonding networks involving water.

DOI： 10.1246/cl.2008.1294

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Development of organocatalysis based on the molecular design of pyrrolidine-bronsted acid catalysts Invited Reviewed

Susumu Saito, Norie Momiyama, Hisashi Yamamoto

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   Vol. 66 ( 8 ) page： 774 - 784   2008.8

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

Proper design of amine-Bronsted acid catalysis has been shown to be effective for achieving high reactivity and selectivity in the asymmetric direct aldol reaction. During the course of this study, two principal approaches have been implemented to create a new type of catalysis: One is derived from Bronsted acid and diamine; the other is pyrrolidine with tetrazole functionality. The developed amine-Bronsted acid catalysts have been found to effectively catalyze the direct aldol reaction of aldehyde, chloral and nitrosobenzene.

Web of Science

Rh(I)-catalyzed aldol-type reaction of organonitriles under mild conditions Reviewed

Akihiro Goto, Kohei Endo, Yu Ukai, Stephan Irle, Susumu Saito

CHEMICAL COMMUNICATIONS   ( 19 ) page： 2212 - 2214   2008.5

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An aldol-type reaction of organonitriles with aldehydes was catalyzed by a Rh(I)(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components.

DOI： 10.1039/b800634b

Web of Science

*RhI-catalyzed Hydration of Organonitriles Under Ambient Conditions Reviewed

Akihiro Goto, Kohei Endo, Susumu Saito

Angew. Chem. Int. Ed.   Vol. 47   page： 3607-3609   2008

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山本尚先生、玉尾皓平先生に日本学士院賞―有機典型元素化合物の反応、物性の開拓に貢献 Invited

斎藤　進、山口茂弘

現代化学   ( 434 ) page： 13   2007

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山本尚先生、玉尾皓平先生日本学士院賞を受賞 Invited

斎藤　進、山口茂弘

有機合成化学協会誌   Vol. 65 ( 5 ) page： 418   2007

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有機触媒を用いる酸－塩基相互作用の制御と有機アニオン種の形成に基づく不斉合成 Invited

斎藤 進

月刊ファインケミカル   Vol. 36 ( 5 ) page： 64-80   2007

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東海から発信する産学官連携のトレンド Invited

大島 康裕、斎藤 進、紫牟田 正則

化学と工業   Vol. 59 ( 7 ) page： 784   2006

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有機触媒を用いる環境調和型合成 Invited

斎藤 進

化学と工業   Vol. 58 ( 9 ) page： 1041-1042   2005

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O-nitroso aldol synthesis: Catalytic enantioselective route to alpha-aminooxy carbonyl compounds via enamine intermediate Invited Reviewed

N Momiyama, H Torii, S Saito, H Yamamoto

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA   Vol. 101 ( 15 ) page： 5374 - 5378   2004.4

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The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Bronsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones.

DOI： 10.1073/pnas.0307785101

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PubMed

Asymmetric vinylogous direct aldol reaction using aluminum tris[2,6-bis(4-alkylphenyl)phenoxide] Invited Reviewed

H Takikawa, K Ishihara, S Saito, H Yamamoto

SYNLETT   ( 4 ) page： 732 - 734   2004.3

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Diastereoselective vinylogous direct aldol reaction was realized by use of chiral alpha,beta-unsaturated esters and aldehydes in the presence of aluminum tris[2,6-bis(4-alkylphenyl)phenoxide]s. The reaction involves novel 1,7-asymmetric induction and direct coupling of an alpha,beta-unsaturated ester with an aldehyde, through in situ deprotonation of the gamma-proton of the ester component by LTMP.

DOI： 10.1055/s-2004-817761

Web of Science

A new method for the preparation of aluminum and titanium tris(2,6-diphenylphenoxide) reagents and their application in organic synthesis Invited Reviewed

A Sato, A Hattori, K Ishihara, S Saito, H Yamamoto

CHEMISTRY LETTERS   Vol. 32 ( 11 ) page： 1006 - 1007   2003.11

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A new method for the preparation of aluminum and titanium trisphenoxides was realized using tetraallyltin or alpha-pinene as a proton-trapping agent. Thus obtained chlorotitanium reagent was converted to the corresponding cation-type reagent, which proved to be an effective catalyst for epoxide rearrangements.

DOI： 10.1246/cl.2003.1006

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Diversity-based strategy for discovery of environmentally benign organocatalyst: diamine-protonic acid catalysts for asymmetric direct aldol reaction Reviewed

M Nakadai, S Saito, H Yamamoto

TETRAHEDRON   Vol. 58 ( 41 ) page： 8167 - 8177   2002.10

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Fifteen different diamines (4-18) and potonic acids have been screened in the catalytic asymmetric direct aldol reaction of three different aldehydes in acetone. These initial studies demonstrated that the secondary-tertiary diamine series is effective with regard to reactivity. In contrast, the primary-tertiary diamines 13 and 14 were proved to be a superb structural module to avoid dehydration. Further investigation led us to a new procedure for the preparation of diamine catalysts for synthetic convenience. This involves diamine-diacid salt 22, which acted not only as a catalyst backbone but also as a TfOH source. Salt 22-diamine 4 catalyst thus prepared was found to exhibit higher reactivity and selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

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Nucleophilic addition of organomagnesiums to aldimines: Scandium triflate (Sc(OTf)(3)) as an effective catalyst Reviewed

S Saito, K Hatanaka, H Yamamoto

SYNLETT   ( 12 ) page： 1859 - 1861   2001.12

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The 1,2-addition of organomagnesium reagents to p-methoxyphenyl(PMP)amine-derived aldimines proceeded effectively in the presence of catalytic amounts of Sc(OTf)(3).

Web of Science

Nucleophilic addition of organomagnesiums to aldimines:: Scandium triflate (Sc(OTf)₃) as an effective catalyst Invited Reviewed

Saito, S; Hatanaka, K; Yamamoto, H

SYNLETT   ( 12 ) page： 1859 - 1861   2001.12

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Diamine-protonic acid catalysts for catalytic asymmetric aldol reaction Reviewed

S Saito, M Nakadai, H Yamamoto

SYNLETT   ( 8 ) page： 1245 - 1248   2001.8

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Four different protonic acids and 15 diamines were screened in the catalytic asymmetric direct aldol reaction of three different aldehydes in acetone.

Web of Science

Asymmetric Mannich-type reactions with a chiral acetate: effect of Lewis acid on activation of aldimine Invited Reviewed

Saito, S; Hatanaka, K; Yamamoto, H

TETRAHEDRON   Vol. 57 ( 5 ) page： 875 - 887   2001.1

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DOI： 10.1016/S0040-4020(00)01042-5

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Asymmetric Mannich-type reactions with a chiral acetate: effect of Lewis acid on activation of aldimine Reviewed

S Saito, K Hatanaka, H Yamamoto

TETRAHEDRON   Vol. 57 ( 5 ) page： 875 - 887   2001.1

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We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of ortho-alkoxy (or ortho-fluoro) aniline-derived aldimines which found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate, which has optically pure 2,6-bis(2-isopropylphenyl)-3,5-dimethylphenol as a chiral auxiliary with axial chirality. A Lewis acid additive is likely to have a complementary role in the pronounced activation of imine functionalities in the Mannich-type addition of the bulky chiral acetate. (C) 2001 Elsevier Science Ltd. All rights reserved.

Web of Science

Polyene Synthesis via Dehydration of Hydroxyenals and -enones: HfCl4_THF_2 as an Effective Catalyst for Di-, Tri-, and Tetraene Formation Reviewed

Susumu Saito, Takashi Nagahara, Hisashi Yamamoto

Synlett     page： 1690-1692   2001

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Novel three-component coupling using aluminum tris(2,6-diphenylphenoxide) (ATPH): The same synthetic strategy leads to trans- and cis-jasmonates Reviewed

Susumu Saito, Satoko Yamazaki, Hisashi Yamamoto

Angewandte Chemie - International Edition   Vol. 40 ( 19 ) page： 3613 - +   2001

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A one-pot three-component coupling involving organolithium reagents, ATPH·cyclopentenone complex, and dihydrofuran·BCl3 complex (see scheme) gives moderate to good yields of the products with selective formation of either the 2,3-cis or 2,3-trans isomer, depending on the nature of the lithium reagent.

DOI： 10.1002/1521-3773(20011001)40:19<3613::AID-ANIE3613>3.0.CO;2-3

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PubMed

Novel Three Component Coupling Using Aluminum Tris(2,6-diphenylphenoxide) (ATPH): Identical Synthetic Strategy leads to trans- and cis-jasmonates Reviewed

Susumu Saito, Satoko Yamazaki, Hisashi Yamamoto

Angew. Chem. Int. Ed.   Vol. 40   page： 3613-3617   2001

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Direct coupling of anilines with aryllead triacetates Reviewed

S Saito, T Kano, Y Ohyabu, H Yamamoto

SYNLETT   ( 11 ) page： 1676 - 1678   2000.11

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The aryl-aryl coupling of aryllead triacetates at the ortho-position of anilines was achieved by simple magnesation of the aniline nitrogen.

Web of Science

Direct coupling of anilines with aryllead triacetates Invited Reviewed

Saito, S; Kano, T; Ohyabu, Y; Yamamoto, H

SYNLETT   ( 11 ) page： 1676 - 1678   2000.11

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Regio- and enantioselective siloxybutylation at the more hindered alpha-site of unsymmetrical ketone using chiral aluminum trisnaphthoxide Reviewed

S Saito, M Nakadai, H Yamamoto

SYNLETT   ( 8 ) page： 1107 - 1110   2000.8

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A regio- and enantioselective siloxybutylation at the more hindered alpha-site of unsymmetrical dialkyl ketones was achieved to give a quarternary carbon center by the combined use of the chiral aluminum trisnaphthoxide (R)-ATBN and a base.

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Asymmetric Mannich-type reactions of aldimines with a chiral acetate Reviewed

S Saito, K Hatanaka, H Yamamoto

ORGANIC LETTERS   Vol. 2 ( 13 ) page： 1891 - 1894   2000.6

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We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of o-alkoxy (or o-fluoro) aniline-derived aldimines which have been found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate. A Lewis acid additive has a complementary role in the pronounced activation of imine functionalities.

DOI： 10.1021/ol000099e

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PubMed

Molecular Recognition of Carbonyl Compounds Using Aluminum Tris(2,6-diphenylphenoxide) (ATPH) : New Regio- and Stereoselective Alkylation of a,b-Unsaturated Carbonyl Compounds. Reviewed

Susumu Saito, Masahito Shiozawa, Takashi Nagahara, Masakazu Nakadai, and Hisashi Yamamoto

J. Am. Chem. Soc.   Vol. 122   page： 7847-7848   2000

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Aluminum Tris(2,6-diphenylphenoxide)-ArCOCl Complex for Nucleophilic Dearomatic Functionalization Reviewed

Susumu Saito, Toshihiko Sone, Masaaki Murase and Hisashi Yamamoto

J. Am. Chem. Soc.   Vol. 122   page： 10216-10217   2000

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実用的な金属試薬、アルミニウム Invited

斎藤　進

ファルマシア   Vol. 36 ( 7 ) page： 610-611   2000

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Li(I), Na(I) and K(I) Lewis Acids

Susumu Saito

Handbook on Lewis Acid, VCH & Wiley     page： 1-67   2000

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実用的な金属試薬、アルミニウム Invited

斎藤 進

ファルマシア   Vol. 36 ( 7 ) page： 610-611   2000

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Asymmetric coupling of phenols with arylleads Reviewed

S Saito, T Kano, H Muto, M Nakadai, H Yamamoto

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 121 ( 38 ) page： 8943 - 8944   1999.9

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Directed aldol condensation Reviewed

S Saito, H Yamamoto

CHEMISTRY-A EUROPEAN JOURNAL   Vol. 5 ( 7 ) page： 1959 - 1962   1999.7

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

The present article covers the progress in directed aldol condensation, which can be divided into three different classes. First, the mixed aldol condensation that uses general acids or bases under protic conditions. Second, stepwise enolization-aldolization sequence that utilizes various metal enolates under aprotic conditions. Third, a novel mixed aldol condensation that makes use of a bulky Lewis acid and a lithium amide under aprotic conditions. The scope and limitation of each of three aldol strategies is discussed.

Web of Science

Novel three component coupling of ketone, cyclic ether and epoxide using aluminum tris(2,6-diphenylphenoxide) (ATPH) Reviewed

S Saito, S Yamazaki, M Shiozawa, H Yamamoto

SYNLETT   ( 5 ) page： 581 - 583   1999.5

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A ketone, cyclic ether, and epoxide are combined in one-pot using aluminum tris(2,6-diphenylphenoxide) (ATPH) and LDA, the latter agent being applied as the trigger for the reaction.

Web of Science

Novel three component coupling of ketone, cyclic ether and epoxide using aluminum tris(2,6-diphenylphenoxide) (ATPH) Invited Reviewed

Saito, S; Yamazaki, S; Shiozawa, M; Yamamoto, H

SYNLETT   ( 5 ) page： 581 - 583   1999.5

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Designer Lewis acid catalysts for selective organic synthesis Reviewed

H Yamamoto, S Saito

PURE AND APPLIED CHEMISTRY   Vol. 71 ( 2 ) page： 239 - 245   1999.2

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

The present paper covers the progress in stereo-, regio-, and chemoselective carbon-carbon bond-forming reactions promoted by structurally well-designed aluminum aryloxides. Compared with conventional Lewis acids, these aluminum reagents strongly coordinate with various oxygen-containing substrates, and the coordination aptitude is strongly affected by the steric environment of the metal ligands. In principle, the carbonyl groups of the bound substrates are electronically activated but sterically deactivated depending on the aluminum reagent and the type of the reaction employed. This review specifically highlights the selective organic reactions using ATPH.

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Aluminum trisphenoxide polymer as a Lewis acidic, solid catalyst Reviewed

S Saito, M Murase, H Yamamoto

SYNLETT   ( 1 ) page： 57 - 58   1999.1

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A newly introduced, solid polymer of an aluminum trisphenoxide has been demonstrated an efficient catalyst for promoting the Diels-Alder reaction of alpha,beta-enals.

Web of Science

Conjugate addition of lithium enolates to aromatic carbonyl compounds complexed with aluminum tris(2,6-diphenylphenoxide) (ATPH) Reviewed

S Saito, T Sone, K Shimada, H Yamamoto

SYNLETT   ( 1 ) page： 81 - 83   1999.1

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Various lithium enolates of esters undergo effective 1,6-addition to aromatic carbonyl compounds in the presence of aluminum tris(2,6-diphenylphenoxide)(ATPH).

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Aluminum trisphenoxide polymer as a Lewis acidic, solid catalyst Invited Reviewed

Saito, S; Murase, M; Yamamoto, H

SYNLETT   ( 1 ) page： 57 - 58   1999.1

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Conjugate addition of lithium enolates to aromatic carbonyl compounds complexed with aluminum tris(2,6-diphenylphenoxide) (ATPH) Invited Reviewed

Saito, S; Sone, T; Shimada, K; Yamamoto, H

SYNLETT   ( 1 ) page： 81 - 83   1999.1

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Mixed crossed aldol condensation between conjugated esters and aldehydes using aluminum tris(2,6-diphenylphenoxide) Reviewed

Susumu Saito, Masahito Shiozawa, Hisashi Yamamoto

Angewandte Chemie - International Edition   Vol. 38 ( 12 ) page： 1769 - 1771   1999

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The combined use of aluminum tris(2,6-diphenylphenoxide) (ATPH) and lithium 2,2,6,6-tetramethylpiperidide (LTMP) has proven to be effective for the mixed crossed aldol condensation between conjugated esters and various aldehydes. An example is shown in Equation (1).

DOI： 10.1002/(SICI)1521-3773(19990614)38:12<1769::AID-ANIE1769>3.0.CO;2-0

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Mixed Aldol Condensation of α, β-Unsaturated Esters with Aldehydes Using Aluminum Tris(2,6-diphenylphenoxide)(ATPH). Reviewed

Susumu Saito, Masahito Shiozawa, Hisashi Yamammoto

Angew. Chem. Int. Ed. Engl.   Vol. 38   page： 1769-1771   1999

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Designer Lewis acids for selective organic synthesis Reviewed

H Yamamoto, A Yanagisawa, K Ishihara, S Saito

PURE AND APPLIED CHEMISTRY   Vol. 70 ( 8 ) page： 1507 - 1512   1998.8

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A variety of Lewis acid reagents were utilized for Diels-Alder, aldol, and ene reactions with high enantioselectivities. The origin of the selectivity of these reactions is discussed.

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Conceptually new directed aldol condensation using aluminum tris(2,6-diphenylphenoxide) Reviewed

S Saito, M Shiozawa, M Ito, H Yamamoto

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 120 ( 4 ) page： 813 - 814   1998.2

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Diastereoselective aldol reaction with an acetate enolate: 2,6-bis(2-isopropylphenyl)-3,5-dimethylphenol as an extremely effective chiral auxiliary Reviewed

S Saito, K Hatanaka, T Kano, H Yamamoto

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 37 ( 24 ) page： 3378 - 3381   1998

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Designer Lewis acid catalysts - bulky aluminium reagents for selective organic synthesis Reviewed

S Saito, H Yamamoto

CHEMICAL COMMUNICATIONS   ( 17 ) page： 1585 - 1592   1997.9

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Sterically hindered aluminium aryloxides have been developed as designer Lewis acid catalysts for stereo-, regio- and chemo-selective carbon-carbon bond-forming reactions. Compared with classical Lewis acids, these aluminium reagents coordinate strongly with various oxygen-containing substrates, and this coordination is affected by the steric environment of their ligands, The carbonyl groups of the bound substrates are either electronically activated or sterically deactivated depending on the aluminium reagent used and the type of reaction, Designer chiral catalysts based on the structure of these bulky aluminium reagents have also been examined.

Web of Science

2,6-bis(2-alkylphenyl)-3,5-dimethylphenol as a new chiral phenol with C-2-symmetry. Application to the asymmetric alkylation of aldehydes Invited Reviewed

Saito, S; Kano, T; Hatanaka, K; Yamamoto, H

JOURNAL OF ORGANIC CHEMISTRY   Vol. 62 ( 16 ) page： 5651 - 5656   1997.8

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DOI： 10.1021/jo970747g

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2,6-bis(2-alkylphenyl)-3,5-dimethylphenol as a new chiral phenol with C-2-symmetry. Application to the asymmetric alkylation of aldehydes Reviewed

S Saito, T Kano, K Hatanaka, H Yamamoto

JOURNAL OF ORGANIC CHEMISTRY   Vol. 62 ( 16 ) page： 5651 - 5656   1997.8

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A new synthetic route to allylsilanes: The reaction of silyllithium reagents with aromatic carbonyl compounds and aluminium tris(2,6-diphenylphenoxide) (ATPH) Invited Reviewed

Saito, S; Shimada, K; Yamamoto, H; deMarigorta, EM; Fleming, I

CHEMICAL COMMUNICATIONS   ( 14 ) page： 1299 - 1300   1997.7

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DOI： 10.1039/a702684f

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A new synthetic route to allylsilanes: The reaction of silyllithium reagents with aromatic carbonyl compounds and aluminium tris(2,6-diphenylphenoxide) (ATPH) Reviewed

S Saito, K Shimada, H Yamamoto, EM deMarigorta, Fleming, I

CHEMICAL COMMUNICATIONS   ( 14 ) page： 1299 - 1300   1997.7

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Conjugate 1,6-addition of silyllithium reagents to aromatic carbonyl substrates in the presence of the carbonyl protector aluminium tris(2,6-diphenylphenoxide) (ATPH) gives allylsilanes.

Web of Science

Regioselective Robinson annulation realized by the combined use of lithium enolates and aluminum tris(2,6-diphenylphenoxide) (ATPH) Reviewed

S Saito, Shimada, I, Y Takamori, M Tanaka, K Maruoka, H Yamamoto

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   Vol. 70 ( 7 ) page： 1671 - 1681   1997.7

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Michael addition of lithium enolates derived from ketones to a variety of alpha, beta-unsaturated ketones was realized in the presence of aluminum tris(2,6-diphenylphenoxide) (ATPH). In this reaction, ATPH can be used as a carbonyl protector of alpha, beta-unsaturated carbonyl substrates upon complexation, which facilitates the regioselective 1,4-addition of lithium enolates to Michael accepters. Similarly, dianions of beta-dicarbonyl compounds undergo Michael addition smoothly using ATPH as an effective promoter of the reaction. Subsequent regioselective, intramolecular aldol condensation was also demonstrated, leading to bicyclic carbon ring systems. Such systems are difficult to obtain by the Robinson annulation usually performed in protic media.

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A new annulation based on a one-pot double Michael addition using aluminum tris(2,6-diphenylphenoxide) (ATPH) Reviewed

S Saito, M Shiozawa, Y Takamori, H Yamamoto

SYNLETT   ( 4 ) page： 359 - +   1997.4

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An annulation system based on sequential inter- and intramolecular Michael addition was realized by the combined use of ketone enolates and aluminum tris(2,6-diphenylphenoxide)(ATPH).

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Selective alkylation of ketones with a bulky aluminum reagent - The THF-TBSOTf system Reviewed

S Saito, M Ito, K Maruoka, H Yamamoto

SYNLETT   ( 4 ) page： 357 - +   1997.4

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Various ketones can be alkylated with tetrahydrofuran (THF) to provide alpha-siloxybutylated ketones in the presence of a bulky aluminum reagent, lithium diisopropylamide (LDA), and t-butyldimethylsilyl triflate (TBSOTf).

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A new annulation based on a one-pot double Michael addition using aluminum tris(2,6-diphenylphenoxide) (ATPH) Invited Reviewed

Saito, S; Shiozawa, M; Takamori, Y; Yamamoto, H

SYNLETT   ( 4 ) page： 359 - +   1997.4

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Highly regioselective alkylation at the more-hindered alpha-site of unsymmetrical ketones by the combined use of aluminum tris(2,6-diphenylphenoxide) and lithium diisopropylamide Reviewed

S Saito, M Ito, H Yamamoto

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 119 ( 3 ) page： 611 - 612   1997.1

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Aluminum tris(4-bromo-2,6-diphenylphenoxide)(ATPH-Br): An effective catalyst for claisen rearrangement Reviewed

S Saito, K Shimada, H Yamamoto

SYNLETT   ( 8 ) page： 720 - +   1996.8

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A new Lewis acidic receptor, aluminum tris(4-bromo-2,6-diphenylphenoxide)(ATPH-Br), is a powerful promoter of the Claisen rearrangement of various allyl vinyl ethers and is effective for controlling the stereochemistry of the resulting rearrangement products.

Web of Science

Aluminum tris(4-bromo-2,6-diphenylphenoxide)(ATPH-Br): An effective catalyst for claisen rearrangement Invited Reviewed

Saito, S; Shimada, K; Yamamoto, H

SYNLETT   ( 8 ) page： 720 - +   1996.8

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Efficient conjugate reduction of alpha,beta-unsaturated carbonyl compounds by complexation with aluminum tris(2,6-diphenylphenoxide) Reviewed

S Saito, H Yamamoto

JOURNAL OF ORGANIC CHEMISTRY   Vol. 61 ( 9 ) page： 2928 - 2929   1996.5

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Retro-Synthetic Analysis

  Vol. 51   page： 34-36   1996

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Selective Organic Synthesis Using Novel Lewis Acidic Receptor

  Vol. 50   page： 58-59   1995

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Molecular Design of aChiral Lewis Acid for Claisen Rearrangement Reviewed

Keiji Maruoka, Susumu Saito, Hisashi Yamammoto

Journal of AmericanChemical Society   Vol. 117   page： 1165   1995

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AsymmetricDiels-Alder Reaction of UnsymmetricalMaleates. A Chemical Access to Chiral, Unsymmetricalcis-Cyclohexene-1,2-di-carboxylates Reviewed

Keiji Maruoka, Matsujiro Akakura, Susumu Saito, Takashi Ooi, Hisashi Yamammoto

Journal of AmericanChemical Society   Vol. 116   page： 6153   1994

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AluminumTris(2,6-diphenylphenoxide) as an Extremely Selective Activator of Less Hindered AldehydeCarbonyl Reviewed

Keiji Maruoka, Susumu Saito, Hisashi Yamammoto

Synlett     page： 439   1994

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Virtually CompleteBlocking of α, β-Unsaturated AlbehydeCarbonyls by Complexation with AluminumTris(2,6-diphenylphenoxide) Reviewed

Keiji Maruoka, Hiroshi Imoto, Susumu Saito, *Hisashi Yamammoto

Journal of AmericanChemical Society   Vol. 116   page： 4131   1994

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Regioncontrolled]2+2[ Cycloaddition of UnsymmetricalFumarates Based on the Discrimination of TwoDifferent Ester Carbonyl with MAD Reviewed

Keiji Maruoka, Susumu Saito, Hisashi Yamammoto

Synlett     page： 197   1993

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Chemoselective Functionalization of More Hindered Aldehyde Carbonyl with Methyl-aluminumBis(2,6-diphenylphenoxide)/Alkyllithium System Reviewed

Keiji Maruoka, Susumu Saito, Arnel B. Concepcion, Hisashi Yamammoto

Journal of AmericanChemical Society   Vol. 115   page： 1183   1993

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A New Strategy forObtaining High Level of Diastereoselectivityin the Asymmetric Diels-Alder Reaction of Chiral Dienophiles Reviewed

Keiji Maruoka, Kei Shiohara, Masataka Oishi, Susumu Saito, Hisashi Yamammoto

Synlett     page： 4321   1993

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Discrimination of TwoDifferent Ester Carbonyl with MAD : Application to the Region and StereocontrolledDiels-Alder Reaction of UnsymmetricalFumarates Reviewed

Keiji Maruoka, Susumu Saito, Hisashi Yamammoto

Journal of AmericanChemical Society   Vol. 114   page： 1089   1992

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Selective Reduction ofMethylenecyclalkane Oxides withDiisobutylaluminum2,6-di-tert-butyl-4-substituted-phenoxide Reviewed

Keiji Maruoka, Susumu Saito, Takashi Ooi, Hisashi Yamammoto

Synlett     page： 255   1991

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A NEW StereoselectiveApproach to Oxygenated Carbocycles : Asymmetric Synthesis of the CyclohexylFragment of FK-506 Reviewed

Keiji Maruoka, Susumu Saito, Takashi Ooi, Hisashi Yamammoto

Synlett     page： 579   1991

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