Nippon Chemical Industrial Co., Ltd.

Chiba University

Aya Koide

Kazuhiro Yoshida

Tsuneo Imamoto

Miwako Nishimura

Youichi Saitoh

Disclosed is a process of preparing an optically active allyl compound, e.g., as represented by formula (III): comprising asymmetrically coupling an allyl compound with an organic nucleophilic compound in the presence of a catalyst. The catalyst is preferably a transition metal complex compound having a phosphine ligand. The phosphine ligand is preferably a 2,3-bis(dialkylphosphino)pyrazine derivative. The pyrazine derivative is preferably a quinoxaline derivative. The transition metal is preferably palladium.

Process of preparing optically active allyl compound

Disclosed is a process of preparing an optically active &#x3b2;-hydroxycarboxylic acid derivative comprising asymmetrically hydrogenating a &#x3b2;-keto compound in the presence of a catalyst comprising a transition metal complex compound having a 2,3-bis(dialkylphosphino)pyrazine derivative as a ligand. The pyrazine derivative is preferably a quinoxaline derivative, and the transition metal is preferably ruthenium. Preferred examples of the quinoxaline derivative are (S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline, (R,R)-bis(tert-butylmethylphosphino)quinoxaline, (S,S)-bis(tert-adamantylmethylphosphino)quinoxaline, and (R,R)-bis(adamantylmethylphosphino)quinoxaline.

Process of preparing optically active &#x3b2;-hydroxycarboxylic acid derivative

An optically-active bis(alkynylphosphino)ethane-borane derivative represented by formula (1):  The derivative (1) is prepared by bromination of, e.g., an (S)-t-butylmethylphosphine-borane, reaction with an alkynyl lithium, deprotonation, followed by oxidative coupling. Deprotection of the derivative (1) by deboranation gives an optically-active bis(alkynylphosphino)ethane derivative useful as a ligand providing an asymmetric catalyst for catalytic asymmetric synthesis. The asymmetric catalyst having the ligand exhibits high selectivity and catalyst activity.

Growing community of inventors

Chiba, Japan

Aya Koide