REGIOCONTROL OF NITRILE OXIDE CYCLOADDITIONS TO ALLYL ALCOHOLS - SYNTHESIS OF 4-SUBSTITUTED AND 4,4-DISUBSTITUTED 5-HYDROXYMETHYL-2-ISOXAZOLINES

被引：61

作者：

KANEMASA, S ^{[1
]}

NISHIUCHI, M ^{[1
]}

WADA, E ^{[1
]}

机构：

[1] KYUSHU UNIV,GRAD SCH ENGN SCI,DEPT MOLEC SCI & TECHNOL INTERDISCIPLINARY,KASUGA,FUKUOKA 816,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(00)91622-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first regiocontrol of nitrile oxide cycloadditions is described. Reaction of benzonitrile oxide with (E)-2-butenol is highly accelerated by the presence of a magnesium alkoxide, and this reaction proceeds in an exclusively regioselective manner to produce 5-hydroxymethyl-4-methyl-3-phenyl-2-isoxazoline as the sole cycloadduct. Synthetic applications to other substituted allyl alcohols are discussed.

引用

页码：1357 / 1360

页数：4

共 6 条

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