β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines

被引：178

作者：

Kawahara, S ^{[1
]}

Nakano, A ^{[1
]}

Esumi, T ^{[1
]}

Iwabuchi, Y ^{[1
]}

Hatakeyama, S ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 17期

关键词：

D O I：

10.1021/ol035102j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Isocupreidine (beta-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic Imines with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-alpha-methylene-beta-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.

引用

页码：3103 / 3105

页数：3