On the regioselectivity in nitrone cycloadditions to γ-oxo α,β-unsaturated esters

被引：13

作者：

Alibés, R

Busqué, F

de March, P ^{[1
]}

Figueredo, M

Font, J

Parella, T

机构：

[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

[2] Univ Autonoma Barcelona, Serv Ressonancia Magnet Nucl, E-08193 Barcelona, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 36期

关键词：

D O I：

10.1016/S0040-4020(98)00628-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-dipolar cycloadditions of the cyclic nitrones 1 and 2 to several gamma-oxo alpha,beta-unsaturated esters, 5-10, are reported. A strong predominance of the regioisomers with the oxygen atom of the dipole attached to the beta-ester position is observed. This high regioselectivity is attributed to steric factors. The reduction of the carbonyl group of some of the major cycloadducts is a good yielding procedure for the preparation of some hydroxylic derivatives that are not formed or obtained only as minor stereoisomers in the cycloadditions of the same nitrones to the corresponding gamma-hydroxy alpha,beta-unsaturated esters. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：10857 / 10878

页数：22

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