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1,3‐dipolar cycloaddition reactions of 1‐aryl‐ N ‐methyl‐2(1 H ‐azol‐1‐yl)‐ethanimine N ‐oxides to olefins
Author(s) -
Mullen George B.,
Bennett Grace A.,
Swift Patricia A.,
Marinyak David M.,
Dormer Peter G.,
Georgiev Vassil St.
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900116
Subject(s) - chemistry , cycloaddition , regioselectivity , diastereomer , stereoselectivity , 1,3 dipolar cycloaddition , aryl , medicinal chemistry , silica gel , column chromatography , organic chemistry , catalysis , alkyl
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.