NEW ONE-STEP PROCESS FOR THE SYNTHESIS OF FUNCTIONALIZED 1,6-DIOXASPIRO[4,5]DECANES

被引：8

作者：

CARRETERO, JC

ROJO, J

DIAZ, N

HAMDOUCHI, C

POVEDA, A

机构：

[1] Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autönoma de Madrid, Cantoblanco

来源：

TETRAHEDRON | 1995年 / 51卷 / 31期

关键词：

D O I：

10.1016/0040-4020(95)00453-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Phenylsulfonyl dihydrofurans 1 were readily prepared by reduction of alpha-phenylsulfonyl-gamma-lactones with DIBAL-H, followed by dehydration with MsCl-Et(3)N. Dihydrofurans 1 were deprotonated with n-BuLi and the resulting alpha-lithiated carbanion reacted with a wide variety of electrophiles. Particularly interesting is its reaction with gamma-lactones because affords 1,6-dioxaspiro[4,5]decanes in good yields in one-step procedure. This new method of synthesis of spiroketals, in non-acid conditions, is thermodynamically controlled and occurs with high stereoselectivity at C-4, C-5 and C-7, but not at C-2.

引用

页码：8507 / 8524

页数：18

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