Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration

被引：98

作者：

Yang, Yang ^{[1
]}

Perry, Ian B. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 31期

基金：

美国国家卫生研究院;

关键词：

BOND-FORMING HYDROGENATION; ASYMMETRIC-SYNTHESIS; CONJUGATE REDUCTION; ACID-DERIVATIVES; PRIMARY ALCOHOLS; ALLYLIC AMINES; ALKYNES; HYDROALKYLATION; HYDROAMINATION; KETONES;

D O I：

10.1021/jacs.6b06299

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The copper-catalyzed intermolecular enantioselective addition of styrenes to imines has been achieved under mild conditions at ambient temperature. This process features the use of styrenes as latent carbanion equivalents via the intermediacy of catalytically generated benzylcopper derivatives, providing an effective means for accessing highly enantiomerically enriched amines bearing contiguous stereocenters. Mechanistic studies shed light on the origin of the preferential styrene hydrocupration in the presence of an imine with the PhBPE-derived copper catalyst.

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页码：9787 / 9790

页数：4

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