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Diversion from Bicyclo[4.2.0]octanol formation through the use of vinyl electrophiles

Loughlin, W., Rowen, C.ORCID: 0000-0003-4490-9542 and Healy, P. (2005) Diversion from Bicyclo[4.2.0]octanol formation through the use of vinyl electrophiles. Synthesis, 2005 (13). pp. 2220-2226.

Link to Published Version: https://doi.org/10.1055/s-2005-869993
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Abstract

Bicyclo[4.2.0]octanols can be obtained from the reaction of phenyl vinyl sulfoxide and the lithium enolate of cyclohexanone under controlled conditions. Diversion to alkylation or Michael-Michael-ring closure was observed when alternative vinyl electrophiles were used. Novel bicyclic disulfones and hydroxyhexahydronaphthalenes were isolated. The use of a vinyl sulfoxide electrophile is crucial to the formation of bicyclo[4.2.0]octanols from simple ketones.

Item Type: Journal Article
Publisher: Thieme
Copyright: © 2005 Georg Thieme Verlag
URI: http://researchrepository.murdoch.edu.au/id/eprint/49202
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