Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

被引：31

作者：

Lin, J ^{[1
]}

Chan, WH ^{[1
]}

Lee, AWM ^{[1
]}

Wong, WY ^{[1
]}

机构：

[1] Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Peoples R China

来源：

TETRAHEDRON | 1999年 / 55卷 / 49期

关键词：

asymmetric alkylation; chiral sultams; kinetic resolution;

D O I：

10.1016/S0040-4020(99)00872-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of enantiomerically pure sultams (+)-1 and (-)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic alpha-bromopropanoate or alpha-bromobutanoate, the enolates of the corresponding N-acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres. (C) 1999 Elsevier Science Ltd. All Fights reserved.

引用

页码：13983 / 13998

页数：16

共 18 条

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