Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional β-isocupreidine derivatives

被引：96

作者：

Abermil, Nacim ^{[1
]}

Masson, Geraldine ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 38期

关键词：

D O I：

10.1021/ja805122j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The aza-MBH reaction of imines 1 and P-naphthyl acrylate 2 in the presence of C-6' modified beta-isocupreidine derivative 1c (0.1 equiv) and beta-naphthol 5 (0.1 equiv) afforded the corresponding (3S)-aza-MBH adducts 4 in high yield and excellent enantiomeric excess. These catalytic conditions allowed the aliphatic imines to be employed for the first time as electrophilic partners of the aza-MBH reaction. The coexistence of two H-bond donors with different acidic strengths was found to be crucial for the observed high enantioselectivity.

引用

页码：12596 / +

页数：3

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