The first general enantioselective catalytic Diels-Alder reaction with simple α,β-unsaturated ketones

被引：422

作者：

Northrup, AB ^{[1
]}

MacMillan, DWC ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 11期

关键词：

D O I：

10.1021/ja017641u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first general approach to enantioselective catalysis of the Diels-Alder reaction with simple ketone dienophiles has been accomplished. The use of iminium catalysis has enabled enantioselective access to a fundamental Diels-Alder reaction variant that has previously been unavailable using chiral Lewis acid catalysis. A new chiral amine catalyst has been developed that allows a variety of monodentate cyclic and acyclic ketones to successfully participate in enantioselective [4 + 2] cycloadditions. A wide spectrum of cyclic and acyclic diene substrates can also be accommodated in this new organocatalytic transformation. A computational model is provided that is in accord with the sense of enantioinduction observed for all reactions conducted during the course of this study. Copyright © 2002 American Chemical Society.

引用

页码：2458 / 2460

页数：3

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