Reactivity of (E)-1-(tert-butyldimethyl)silyloxy-3,3-bis(tributylstannyl)-propene: Syn selective S-E' addition to aldehydes

被引：28

作者：

Madec, D ^{[1
]}

Ferezou, JP ^{[1
]}

机构：

[1] ECOLE POLYTECH,CNRS,DCSO,SYNTH ORGAN LAB,F-91128 PALAISEAU,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(97)01559-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of (E)-1-(tert-butyldimethyl)silyloxy-3,3-bis(tributylstannyl)propene 1 as potential 1,3 dianion equivalent has been investigated. Condensation with aldehydes 4a-h, in presence of BF3OEt2, afforded in high yields the mono-protected diols 5a-h exhibiting an exclusive E configuration of the vinyltin residue. Good to high syn selectivities have been measured, in agreement with an S-E' addition mechanism. Further transformation of the resulting vinyltin moiety of these diols into various functionalities has been successfully tested. (C) 1997 Elsevier Science Ltd.

引用

页码：6661 / 6664

页数：4