CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes

被引：45

作者：

Zhou, Yujing ^{[1
]}

Bandar, Jeffrey S. ^{[1
]}

Liu, Richard Y. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 02期

基金：

美国国家卫生研究院;

关键词：

PRIMARY ALLYLIC ALCOHOLS; CONJUGATE REDUCTION; TRANSFER HYDROGENATION; MICHAEL ADDITION; DECARBOXYLATIVE HYDROFORMYLATION; ENANTIOSELECTIVE ISOMERIZATION; SUPRAMOLECULAR CATALYST; ARYLBORONIC ACIDS; FORMAL SYNTHESIS; COPPER HYDRIDE;

D O I：

10.1021/jacs.7b12260

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The copper hydride (CuH)-Catalyzed enantioselective reduction of alpha,beta-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of beta-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.

引用

收藏

页码：606 / 609

页数：4

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