Rhodium-Catalyzed Asymmetric Arylation of Cyclic N-Sulfonyl Aryl Alkyl Ketimines: Efficient Access to Highly Enantioenriched α-Tertiary Amines

被引：66

作者：

Jiang, Tao ^{[1
]}

Wang, Zheng ^{[1
]}

Xu, Ming-Hua ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 03期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE ARYLATION; NUCLEOPHILIC ALLYLATION; SULFUR-OLEFINS; CHIRAL LIGANDS; IMINES; TOSYLARYLIMINES; TOSYL;

D O I：

10.1021/ol503537w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple catalyst system of Rh(I)/sulfur-olefin with exceptional catalytic performance has been developed for the highly enantioselective arylation of cyclic N-sulfonyl aryl alkyl ketimines with arylboroxines/arylboronic acids. Optically active a-arylalkyl-substituted benzosultams and benzosulfamidates which are generally difficult to obtain were easily prepared with excellent stereocontrol (up to 99.9% ee). The synthetic utility of the approach was demonstrated by the facile construction of NMDA antagonist FR115427 and benzoxazinone derivatives. This protocol offers new opportunities for the efficient synthesis of diverse chiral a-tertiary amines.

引用

页码：528 / 531

页数：4

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