Regioselective and stereoselective reductive cleavage of 1,7-dioxaspiro[5.5]undecane alcohols

被引：31

作者：

Crimmins, MT

Rafferty, SW

机构：

[1] Venable and Kenan Labs. of Chemistry, Univ. of N. Carolina at Chapel Hill, Chapel Hill

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 32期

基金：

英国惠康基金; 美国国家卫生研究院;

关键词：

reductive cleavage; spiroketals; 1,7-dioxaspiro[5.5]undecanes; tetrahydropyrans;

D O I：

10.1016/0040-4039(96)01196-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid-promoted triethylsilane reduction of 6,6-spiroketol alcohols produces cis-2,6-disubstituted tetrahydropyrans with excellent regioselectivity and stereocontrol. An appended alcohol allows bidentate coordination of the Lewis acid to selectively activate one CO bond of the anomeric center toward reductive cleavage. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：5649 / 5652

页数：4