Enantioselective 1,3-dipolar cycloaddition of nitrones with ethyl vinyl ether: The difference between bronsted and Lewis acid catalysis

被引：170
作者：
Jiao, Peng [1 ]
Nakashima, Daisuke [1 ]
Yamamoto, Hisashi [1 ]
机构：
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 13期
关键词：
asymmetric catalysis; cycloaddition; organocatalysis; phosphoramides;
D O I：
10.1002/anie.200705314
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Brønsted and Lewis face off: A new chiral N-triflyl phosphoramide is used for asymmetric 1,3-dipolar cycloaddition of diaryl nitrones to ethyl vinyl ether to give the endo products in up to 93% ee (see scheme; Tf = trifluoromethanesulfonyl; Ad = adamantyl). The structure of the chiral phosphoramide was confirmed by X-ray crystallographic analysis. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：2411 / 2413
页数：3
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