Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals

被引：103

作者：

White, Nicholas A. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 32期

关键词：

N-HETEROCYCLIC-CARBENE; STEREOSELECTIVE-SYNTHESIS; HOMOENOLATE ADDITIONS; GAMMA-BUTYROLACTONES; BETA-HYDROXYLATION; DIRECT ANNULATIONS; ALDEHYDES;

D O I：

10.1021/jacs.5b06390

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented N-heterocyclic carbene (NHC)-catalyzed annulation of enals to form 3,4-disubstituted cyclopentanones has been discovered. Aryl enals undergo dimerization in the presence of a single-electron oxidant to form C-2 symmetric cyclopentanones. A cross-reaction has also been developed, allowing for the synthesis of differentially substituted cyclopentanones. Mechanistically, the reaction is thought to proceed through radical intermediates, further establishing the synthetic utility of this class of reactivity.

引用

页码：10112 / 10115

页数：4

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