Novel bifunctional chiral thiourea catalyzed highly enantioselective aza-Henry reaction

被引：84
|
作者：
Wang, Chungui [1 ]
Zhou, Zhenghong [1 ]
Tang, Chuchi [1 ]
机构：
[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 09期
关键词：
D O I：
10.1021/ol8003035
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel bifunctional chiral thiourea organocatalyst bearing a glycosyl scaffold and a tertiary amino group was synthesized starting from readily available alpha-D-glucose. This thiourea was proven to be an effective organocatalyst for the asymmetric aza-Henry reaction between N-Boc imines and nitromethane. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 99.8% ee). In addition, the reaction of nitroethane also proceeded smoothly with excellent enantioselectivity, albeit with low to good diastereoselectivities.
引用
收藏
页码：1707 / 1710
页数：4
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