General stereoselective synthesis of (E)-exo-alkylidene tetrahydrofurans via base-mediated cyclization of hydroxyl propargylic sulfones

被引：14

作者：

Dai, WM ^{[1
]}

Lee, MYH ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Peoples R China

来源：

TETRAHEDRON | 1998年 / 54卷 / 41期

关键词：

D O I：

10.1016/S0040-4020(98)00730-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The base-promoted cyclization of a number of phenyl propargylic sulfones possessing a hydroxyl group afforded 5-substituted (E)-2-[(benzenesulfonyl)methylene]tetrahydrofurans 3 in >80% yield. The phenyl allenic sulfone, formed by isomerization of the phenyl propargylic sulfone under the basic conditions, is attacked by the internal alkoxide to give an allylic anion which undergoes protonation to form the conjugated exo double bond. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：12497 / 12512

页数：16

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