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.
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收藏
页码：8507 / 8524
页数：18
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