N-Heterocyclic-Carbene-Catalyzed Asymmetric Oxidative Hetero-Diels-Alder Reactions with Simple Aliphatic Aldehydes

被引：150

作者：

Zhao, Xiaodan ^{[1
]}

Ruhl, Kyle E. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 49期

关键词：

asymmetric catalysis; cycloaddition; lactams; N-heterocyclic carbene; oxidation; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; ENALS; ESTERS; AMIDATION; ACYLATION; ACYL;

D O I：

10.1002/anie.201206490

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient enantioselective approach to form trans lactams and cis lactones in up to 98 % yield with greater than 99 % ee, and greater than 20:1 d.r. using simple aliphatic aldehydes has been developed. The process involves a new pathway to generate enolate intermediates from aliphatic aldehydes by oxidation and deprotonation. NHC=N-heterocyclic carbene, Ts=4-toluenesulfonyl. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12330 / 12333

页数：4

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