Faculty Profiles - ISHIHARA Kazuaki

Papers - ISHIHARA Kazuaki

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Enantioselective Conjugate Hydrocyanation of alpha,beta-Unsaturated N-Acylpyrroles Catalyzed by Chiral Lithium(I) Phosphoryl Phenoxide Reviewed

Manabu Hatano, Katsuya Yamakawa, Kazuaki Ishihara

ACS CATALYSIS Vol. 7 ( 10 ) page： 6686 - 6690 2017.10

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

Enantioselective conjugate hydrocyanation of alpha,beta-unsaturated N-acylpyrroles with the combined use of Me3SiCN, LiCN, and HCN has been developed in the presence of a chiral lithium(I) phosphoryl phenoxide catalyst. This reaction is useful for a variety of N-acylpyrroles, including previously unreported substrates, such as heteroaryl and halogen-substituted N-cinnamoylpyrroles. A gram-scale reaction and subsequent transformations to a (R)-succinate, (S)paraconic acid, and (R)-baclofen demonstrate an entry for the practical synthesis of optically active beta-substituted gamma-amino butyric acids (GABA).

DOI： 10.1021/acscatal.7b02551

Web of Science

Design of Boronic Acid-Base Complexes as Reusable Homogeneous Catalysts in Dehydrative Condensations between Carboxylic Acids and Amines Reviewed

Yanhui Lu, Ke Wang, Kazuaki Ishihara

ASIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 6 ( 9 ) page： 1191 - 1194 2017.9

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

Two novel boronic acid-base complexes were developed as reusable homogeneous catalysts for amide condensation. First, quaternary ammonium resin-bound boronates were shown to be effective catalysts that might release free boronic acids during reactions and could be regenerated afterwards. Next, a 1:1 mixture of 3,5-dinitro-4-tolueneboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) or 4-(N,N,-dimethylamino)pyridine (DMAP) cooperatively promoted amide formation and precipitated as an acid-base solid complex after cooling. These inexpensive and reusable complexes may be useful in large-scale process chemistry.

DOI： 10.1002/ajoc.201700194

Web of Science

Enantioselective cycloaddition of styrenes with aldimines catalyzed by a chiral magnesium potassium binaphthyldisulfonate cluster as a chiral Brønsted acid catalyst Reviewed

Manabu Hatano, Keisuke Nishikawa, Kazuaki Ishihara

Journal of the American Chemical Society Vol. 139 ( 25 ) page： 8424-8427 2017.5

4,5-Dimethyl-2-Iodoxybenzenesulfonic Acid Catalyzed Site-Selective Oxidation of 2-Substituted Phenols to 1,2-Quinols Reviewed

Muhammet Uyanik, Tatsuya Mutsuga, Kazuaki Ishihara

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 56 ( 14 ) page： 3956 - 3960 2017.3

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

A site-selective hydroxylative dearomatization of 2-substituted phenols to either 1,2-benzoquinols or their cyclodimers, catalyzed by 4,5-dimethyl-2-iodoxybenzenesulfonic acid with Oxone, has been developed. Natural products such as biscarvacrol and lacinileneC methyl ether could be synthesized efficiently under mild reaction conditions. Furthermore, both the reaction rate and site selectivity could be further improved by the introduction of a trialkylsilylmethyl substituent at the 2-position of phenols. The corresponding 1,2-quinols could be transformed into various useful structural motifs by [4+2] cycloaddition cascade reactions.

DOI： 10.1002/anie.201612463

Web of Science

PubMed

Enantioselective synthesis of masked benzoquinones using designer chiral hypervalent organoiodine(III) catalysis Reviewed

Muhammet Uyanik, Niiha Sasakura, Masahiro Mizuno, Kazuaki Ishihara

ACS Catalysis Vol. 7 ( 1 ) page： 872-876 2017.2

Design of High Performance Catalysts Based on Acid-Base Combination Chemistry Invited Reviewed

Kazuaki Ishihara

Vol. 75 ( 2 ) page： 98-110 2017.2

Design of High Performance Catalysts Based on Acid-Base Combination Chemistry

Ishihara Kazuaki

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN Vol. 75 ( 2 ) page： 6 - 18 2017.2

AMMONIUM HYPOIODITE-CATALYZED PEROXIDATIVE DEAROMATIZATION OF PHENOLS Reviewed Open Access

Muhammet Uyanik, Kohei Nishioka, Kazuaki Ishihara

HETEROCYCLES Vol. 95 ( 2 ) page： 1132 - 1147 2017.1

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

Here, we report the first transition metal-free peroxidative dearomatization of phenols using hypoiodite catalysis with TBHP. Hypoiodite salts are generated in situ from the corresponding quaternary ammonium iodides in the presence of TBHP, and the oxidative coupling reaction proceeds efficiently under mild conditions. The dearomatized products are versatile synthetic intermediates for further synthetic transformations to various complex structures including heterocycles. As a demonstration, the further oxidation of the unsaturated peroxide with TBHP afforded the corresponding peroxy epoxide in good yield.

DOI： 10.3987/COM-16-S(S)84

Open Access

Web of Science

Chiral hypervalent organoiodine-catalyzed enantioselective oxidative spirolactonization of naphthol derivatives Reviewed

Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara

J. Org. Chem. Vol. 82 ( 22 ) page： 11946 - 11953 2017

Chiral Quaternary Ammonium Hypoiodite Catalysis Invited Reviewed

Vol. 45 ( 12 ) page： 16-24 2016.12

Regioselective 1,4- and 1,6-conjugate additions of Grignard reagent-derived organozinc(II)ates to poly-conjugated esters Reviewed

Manabu Hatano, Mai Mizuno, Kazuaki Ishihara

Organic Letters Vol. 18 ( 18 ) page： 4462-4465 2016.9

キラルビナフチルジスルホン酸(BINSA)を用いる精密分子設計 Invited Reviewed

波多野学、石原一彰

化学工業 Vol. 67 ( 9 ) page： 660-667 2016.9

Enantioselective bromocyclization of 2-gernaylphenols induced by chiral phosphite-urea bifunctional catalysts Reviewed

Yasuhiro Sawamura, Yoshihiro Ogura, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

Chem. Commun. Vol. 52 ( 36 ) page： 6068-6071 2016.3

Development of Highly Active Boron Lewis Acid-Assisted Chiral Phosphoric Acid Catalysts Based on the Cooperative Acid-Base Functions Invited Reviewed

Vol. 45 ( 2 ) page： 24-32 2016.2

Enantioselective Diels-Alder reaction induced by chiral supramolecular Lewis acid catalysts based on CN···B and PO···B coordination bonds Invited Reviewed

Manabu Hatano, Kazushi Hayashi, Tatsuhiro Sakamoto, Yuma Makino, Kazuaki Ishihara

Synlett Vol. 27 ( 7 ) page： 1061-1067 2016.2

Enantioselective cyanosilylation of ketones with extremely reactive lithium(I) dicyanotrimethylsilicate(IV) catalyzed by chiral lithium(I) phosphoryl phenoxide Reviewed

Manabu Hatano, Katsuya Yamakawa, Tomoaki Kawai, Takahiro Horibe, Kazuaki Ishihara

Angew. Chem. Int. Ed. Vol. 55 ( 12 ) page： 4021-4025 2016.2

Chiral ammonium hypoiodite salt-catalyzed enantioselective oxidative cycloetherification to 2-acyl tetrahydrofurans Reviewed

Muhammet Uyanik, Hiroki Hayashi, Hirokazu Iwata, Kazuaki Ishihara

Chem. Lett. Vol. 45 ( 3 ) page： 353-355 2016.1

Enantioselective cyano-alkoxycarbonylation of α-oxoesters promoted by Brønsted acid-Lewis base cooperative catalysts Reviewed

Kazuaki Ishihara, Yoshihiro Ogura

Org. Lett. Vol. 17 ( 24 ) page： 564-570 2015.12

Structurally defined molecular hypervalent iodine catalysts for intermolecular enantioselective reactions Reviewed

Stefan Haubenreisser, Thorsten H. Wöste, Claudio Martínez, Kazuaki Ishihara, Kilian Muñiz

Angew. Chem. Int. Ed. Vol. 55 ( 1 ) page： 413-417 2015.11

Boronic acid-DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines Reviewed

Kazuaki Ishihara, Yanhui Lu

Chem. Sci. Vol. 7 ( 2 ) page： 1276-1280 2015.11

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Papers - ISHIHARA Kazuaki