Highly efficient asymmetric vinylogous Mannich reaction induced by O-pivaloylated D-galactosylamine as the chiral auxiliary

被引：16
|
作者：
Yu, Jipan
Miao, Zhiwei [1 ]
Chen, Ruyu
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 06期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; STRECKER SYNTHESIS; MICHAEL REACTION; ALDOL REACTION; ACIDS; ADDITIONS; ALPHA; METHODOLOGY; CATALYST;
D O I：
10.1039/c0ob01048k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The diastereospecific formation of beta-N-glycoside-linked alpha-amino-2(5H)-furanone has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and ZnCl2 center dot Et2O as a promoter in Et2O. Imines 3 of aromatic compounds and trimethylsiloxyfuran 4 were converted to N-galactosyl alpha-amino-2(5H)-furanone 5, giving ratios of diastereomers higher than 20:1. This procedure provides rapid access to biologically important gamma-butenolide derivatives.
引用
收藏
页码：1756 / 1762
页数：7
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