α,β-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-Based catalytic asymmetric diels-alder reaction in water

被引:114
作者
Boersma, Arnold J. [1 ]
Feringa, Ben L. [1 ]
Roelfes, Gerard [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
关键词
D O I
10.1021/ol7015274
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha,beta-Unsaturated 2-acyl imidazoles are a novel and practical class of dienophiles for the DNA-based catalytic asymmetric Diels-Alder reaction in water. The Diels-Alder products are obtained with very high diastereoselectivities and enantioselectivities in the range of 83-98%. The catalytic reaction was performed on a 1.0 mmol scale, and the imidazole auxiliary was removed readily.
引用
收藏
页码:3647 / 3650
页数:4
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