The effect of the acidifying group on the regioselectivity of the base-induced ring opening of hetero-oxabicyclic [3.2.1] and [3.3.1] systems

被引：8

作者：

Lautens, M ^{[1
]}

Fillion, E ^{[1
]}

Sampat, M ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(98)00052-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unsymmetrical 8-oxa-3-thiabicyclo[3.2.1]octane and 9-oxa-3-thiabicyclo[3.3.1]nonane underwent highly regioselective base-induced elimination but low selectivity was observed for the sulfonyl and the aza-oxa systems. A correlation between the regioselectivity of the reaction and the proton undergoing abstraction (i.e. equatorial vs. the axial proton) was made. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1501 / 1504

页数：4