Faculty Profiles - SAITO, Susumu

Papers - SAITO, Susumu

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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

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

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

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

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

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

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

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

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

Web of Science

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

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

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

Web of Science

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

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

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

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

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

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

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

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

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

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

Language：English Publishing type：Research paper (scientific journal) Publisher：NATL ACAD SCIENCES

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

Web of Science

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

Language：English Publishing type：Research paper (scientific journal) Publisher：GEORG THIEME VERLAG KG

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

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

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

Web of Science

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

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

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.

Web of Science

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

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

Saito, S; Hatanaka, K; Yamamoto, H

SYNLETT ( 12 ) page： 1859 - 1861 2001.12

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