Sulfoxide covalent catalysis: Application to glycosidic bond formation

被引：35

作者：

Boebel, TA ^{[1
]}

Gin, DY ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 47期

关键词：

glycosylation; homogeneous catalysis; reaction mechanisms; sulfonylation; synthetic methods;

D O I：

10.1002/anie.200352761

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A versatile glycosylation reaction is used to establish the process of sulfoxide covalent catalysis. Hemiacetals are activated by benzenesulfonic anhydride and a dialkyl sulfoxide catalyst, nBu2SO, for coupling with various nucleophiles (Nu; see scheme, TTBP=2,4,6-tri-tert-butylpyridine). The sulfoxide catalyst functions uniquely in three capacities, first as an 0 nucleophile, then as a S+ electrophile, and finally as a leaving group to fulfill turnover.

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页码：5874 / 5877

页数：4

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