The importance of iminium geometry control in enamine catalysis: Identification of a new catalyst architecture for aldehyde-aldehyde couplings

被引:141
作者
Mangion, IK [1 ]
Northrup, AB [1 ]
MacMillan, DWC [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
关键词
aldehydes; aldol reaction; nitrogen heterocycles; organocatalysis; synthetic methods;
D O I
10.1002/anie.200461851
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Central to the design of a new organocatalyst system for aldehyde-aldehyde aldol reactions is the necessity of iminium geometry control during the enamine addition step (see scheme). Significant structural variation in both the aldol donor and aldol acceptor are possible while maintaining high reaction efficiency and enantioselectivity. TFA=trifluoroacetic acid.
引用
收藏
页码:6722 / 6724
页数:3
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