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
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
收藏
页码:2458 / 2460
页数:3
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