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On the stereochemistry of anion-accelerated [1,3]-sigmatropic rearrangement of 2-vinylcyclobutanols

โœ Scribed by Se-Ho Kim; Sung Yun Cho; Jin Kun Cha

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
83 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Stereochemical studies on the oxyanion-accelerated [1,3]-sigmatropic rearrangement reactions of nonracemic cis-and trans-2-(1-cyclohexenyl)cyclobutanols are described. Epimerization of cis-2-(1-cyclohexenyl)cyclobutanol to the trans-isomer at -20ยฐC was found to proceed with predominant retention of configuration, the degree of which was enhanced by an increasing amount of 18-crown-6.

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