Reversal of diastereoselectivity of nitrile oxide 1,3-dipolar cycloadditions by Mg(II).: Acceleration of cycloaddition by microwave irradiation

被引：34

作者：

Micúch, P

Fisera, L ^{[1
]}

Cyranski, MK

Krygowski, TM

Krajcík, J

机构：

[1] Slovak Univ Technol Bratislava, Dept Organ Chem, Bratislava 81237, Slovakia

[2] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland

来源：

TETRAHEDRON | 2000年 / 56卷 / 30期

关键词：

cycloaddition; diastereoselection; nitrile oxides; microwave heating; isoxazolines;

D O I：

10.1016/S0040-4020(00)00454-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions of mesitonitrile oxide to Baylis-Hillman adducts (beta-hydroxy-alpha-methylene esters) proceed regioselectively in good yields. Addition of Grignard reagent reverses the diastereoselectivity of the cycloaddition. Microwave irradiation strongly accelerates the reaction with only a small effect on its diastereoisomeric excess. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5465 / 5472

页数：8

共 19 条

[1] 1,3-DIPOLAR CYCLOADDITIONS TO BAYLIS-HILLMAN ADDUCTS - RATIONALE FOR THE OBSERVED DIASTEREOSELECTIVITY [J].