Probing the "additive effect" in the proline and proline hydroxamic acid catalyzed asymmetric addition of nitroalkanes to cyclic enones

被引：29

作者：

Hanessian, S ^{[1
]}

Govindan, S ^{[1
]}

Warrier, JS ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

CHIRALITY | 2005年 / 17卷 / 09期

关键词：

organocatalysis; proline; proline hydroxamic acid; piperazine; conjugate addition;

D O I：

10.1002/chir.20201

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The effect of chirality and steric bulk of 2,5-disubstituted piperazines as additives in the conjugate addition of 2-nitropropane to cyclohexenone, catalyzed by L-proline, was investigated. Neither chirality nor steric bulk affects the enantioselectivity of addition, which gives 86-93% ee in the presence of achiral and chiral nonracemic 2,5-disubstituted piperazines. Proline hydroxamic acid is shown for the first time to be an effective organocatalyst in the same Michael reaction.

引用

页码：540 / 543

页数：4

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