Unexpected transformations:: from 5-glyco-4-nitrocyclohexenes to bicyclic [3.3.1] oximes through isoxazoline N-oxides

被引：11

作者：

Gil, MV ^{[1
]}

Román, E ^{[1
]}

Serrano, JA ^{[1
]}

机构：

[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 17期

关键词：

nitro compounds; nitroglycocycloalkanes; isoxazoline N-oxides; cyclic nitronic esters; oximes;

D O I：

10.1016/S0040-4039(00)00354-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 5-glyco-4-nitrocyclohexenes with excess or equimolar sodium methoxide gave deacetylated sodium nitronates which, on reaction with Ac2O/py, led to chiral isoxazoline N-oxides (cyclic nitronic esters). Depending on the configuration of their respective sugar side-chains, base-catalyzed deacetylation of these nitronate esters yielded either a bicyclic [3.3.1] oxime or a deacetylated isoxazoline N-oxide. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3221 / 3224

页数：4

共 23 条

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