Secondary and tertiary alcohols as nucleophiles in the stereospecific synthesis of substituted tetrahydrofurans by cyclisation of 1,3-diols with phenylsulfanyl migration

被引：16
|
作者：
Eames, J [1 ]
delasHeras, MA [1 ]
Warren, S [1 ]
机构：
[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 23期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/0040-4039(96)00737-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rearrangement of a series of 4-phenylsulfanyl-1,3-diols with TsOH gives tetrahydrofurans stereospecifically and in high yield even if the nucleophile is a secondary or tertiary alcohol. We discuss the stereochemistry and acceptable substution patterns of the diols which will carry out this reaction and define their limits. (C) 1996 Elsevier Science Ltd.
引用
收藏
页码：4077 / 4080
页数：4
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