P-isocupreidine-catalyzed asymmetric Baylis-Hillman reactions

被引：16

作者：

Hatakeyama, Susumi ^{[1
]}

机构：

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

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2006年 / 64卷 / 11期

关键词：

D O I：

10.5059/yukigoseikyokaishi.64.1132

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioselective asymmetric Baylis-Hillman reactions employing (3R,8R,9S)-10,11-dihydro-3,9-epoxy-6'-hydroxy-cinchonane, beta-isocupreidine (beta-ICD), as a chiral amine catalyst and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) as an activated alkene are described for aldehydes including chiral N-Boc-alpha-amino aldehydes and aromatic N-diphenylphosphinoyl imines. The key features of this beta-ICD-HFIPA method and a plausible reaction mechanism governed by hydrogen bonding are presented.

引用

页码：1132 / 1138

页数：7

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