Highly Asymmetric NHC-Catalyzed Hydroacylation of Unactivated Alkenes

被引：158

作者：

Piel, Isabel ^{[1
]}

Steinmetz, Marc ^{[1
]}

Hirano, Keiichi ^{[2
]}

Froehlich, Roland ^{[1
]}

Grimme, Stefan ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

[2] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 21期

关键词：

enantioselective catalysis; hydroacylation; N-heterocyclic carbenes; organocatalysis; Stetter reaction; INTERMOLECULAR STETTER REACTION; N-HETEROCYCLIC CARBENES; COPE-TYPE HYDROAMINATION; ENANTIOSELECTIVE CONSTRUCTION; CONJUGATE UMPOLUNG; ALPHA; ALPHA-DISUBSTITUTED CYCLOPENTENES; QUATERNARY STEREOCENTERS; GAMMA-BUTYROLACTONES; DIRECT ANNULATIONS; TRIAZOLIUM SALTS;

D O I：

10.1002/anie.201008081

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

NHC-catalysis proto(n)type: The title reaction produces 21 different chroman-4-one-type products in good yields and excellent enantioselectivities, in each case building up a new all-carbon quaternary stereocenter (see scheme). Based on DFT calculations a mechanistic scenario involving proton transfer, possible transition states, and a mode of enantioinduction is presented. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4983 / 4987

页数：5

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