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1,3-dipolar cycloaddition reactions of 1-aryl-N-methyl-2(1H-azol-1-yl)-ethanimineN-oxides to olefins

✍ Scribed by Mullen, George B. ;Bennett, Grace A. ;Swift, Patricia A. ;Marinyak, David M. ;Dormer, Peter G. ;Georgiev, Vassil St.

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 292 KB
Volume: 1990
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199019900116

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✦ Synopsis

Abstract

The regio‐ and stereoselectivity of the 1,3‐dipolar cycloaddition reaction of 1‐aryl‐N‐methyl‐2‐(1__H__‐azol‐1‐yl)ethanimine N‐oxides 6 to monosubstituted olefins 7 were investigated. The reaction is regioselective, leading to the corresponding C‐5 substituted isoxazolidines 8/9 as cis/trans diastereomeric mixtures. The cis isomers, which are the predominant species of the mixtures, are readily separated by flash chromatography on neutral silica gel.

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