Stereoselective glycosylation reactions with chiral auxiliaries

被引：129

作者：

Kim, JH ^{[1
]}

Yang, H ^{[1
]}

Boons, GJ ^{[1
]}

机构：

[1] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 06期

关键词：

anomeric control; carbohydrates; chiral auxiliaries; glycosides; glycosylation;

D O I：

10.1002/anie.200461745

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Good neighbors: A chiral auxiliary is used for the first time to control the anomeric selectivity of glycosylation reactions. In this approach, upon treatment with an activator A+, neighboring-group participation pation of an (S)-ethoxycarbonylbenzyl auxiliary at C2 leads to the formation of 1,2-cis glycosides, probably via a transfused ethyloxonium ion intermediate (see scheme).

引用

页码：947 / 949

页数：3

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