Ishihara World: Rational Design of High-Performance Catalysts

Based on Acid–Base Combination Chemistry

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Selenium–Iodine Cooperative Catalyst for Chlorocyclization of Tryptamine Derivatives

Takahiro Horibe, Shuhei Ohmura, and Kazuaki Ishihara*

Org. Lett. 2017, ASAP.

Publication Date (Web): September 28, 2017 (Letter)
DOI: 10.1021/acs.orglett.7b02613

Chiral Hypervalent Organoiodine-Catalyzed Enantioselective Oxidative Spirolactonization of Naphthol Derivatives

Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara*

J. Org. Chem., 2017, Article ASAP
DOI: 10.1021/acs.joc.7b01941  Publication Date (Web): September 19, 2017

Enantioselective Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles Catalyzed by Chiral Lithium(I) Phosphoryl Phenoxide

Manabu Hatano, Katsuya Yamakawa, Kazuaki Ishihara*
ACS Catal. 2017, 7, 6686-6690.
Publication Date (Web): August 30, 2017

Enantioselective conjugate hydrocyanation of α,β-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 β-substituted γ-aminobutyric acids (GABA).

▼Cover Feature:  Design of Boronic Acid–Base Complexes as Reusable Homogeneous Catalysts in Dehydrative Condensations between Carboxylic Acids and Amines

Yanhui Lu, Ke Wang and Kazuaki Ishihara*

Asian J. Org. Chem. 2017, 7, 1111 (Special Issue: 5th Anniversary Board Member Issue)
Version of Record online: 24 AUG 2017 | DOI: 10.1002/ajoc.201700311

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

Yanhui Lu, Ke Wang, and Kazuaki Ishihara*

Asian J. Org. Chem. 2017, 7, 1191-1194 (Special Issue: 5th Anniversary Board Member Issue)
Version of Record online: 17 MAY 2017

Enantioselective Cycloaddition of Styrenes with Aldimines Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster as a Chiral Brønsted Acid Catalyst

Manabu Hatano, Keisuke Nishikawa, Kazuaki Ishihara*
J. Am. Chem. Soc. 2017, 139(25), 8424–8427.
Publication Date (Web): May 30, 2017

A chiral magnesium potassium binaphthyldisulfonate cluster, as a chiral Brønsted acid catalyst, was shown to catalyze an enantioselective cycloaddition of styrenes with aldimines for the first time. The strong Brønsted acidity of the catalyst precursors, which might dissolve drying agents and take up the leached Mg2+ and K+, serendipitously led to good enantioselectivity. Mechanistic aspects were supported by X-ray and ESI-MS analysis of the catalyst and a kinetics study of the reaction. Useful transformations to optically active 1,3-amino alcohols on a gram scale were also demonstrated.

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ISHIHARA GROUP

国立大学法人 東海国立大学機構

名古屋大学

大学院工学研究科 有機・高分子化学専攻(工学部 化学生命工学科)
有機化学講座

触媒有機合成学研究グループ

〒464-8603 名古屋市千種区不老町

B2-3(611)

 

Laboratory of Catalysis in Organic Synthesis, Research Group of Molecular Chemistry, Graduate Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering (Undergraduate Department of Chemistry and Biotechnology, School of Engineering), Nagoya University

Tokai National Higher Education and Research System

B2-3(611), Furo-cho, Chikusa, Nagoya 464-8603, Japan