Competition of deprotonation and tin-lithium exchange in the generation of a glycosyl dianion

被引：14

作者：

Hoffmann, M ^{[1
]}

Kessler, H ^{[1
]}

机构：

[1] TECH UNIV MUNICH,INST ORGAN CHEM & BIOCHEM,D-85747 GARCHING,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(97)00260-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The deprotonation and the tin-lithium exchange of the glycosylstannane 1 are not decoupled when BuLi is used. Deuteration experiments show that the side product 2H (glycitol) is formed during the deprotonation/transmetallation reaction sequence and not by subsequent protonation of the glycosyl dianion. Decoupling of the two reaction steps is possible by using MeLi*LiBr for deprotonation and BuLi for tin-lithium exchange. The described procedure optimizes the preparation of a beta-lithium-configurated glycosyl dianion by preventing the reduction side reaction. (C) 1997 Elsevier Science Ltd.

引用

页码：1903 / 1906

页数：4

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