Synthesis 2005(13): 2264-2266  
DOI: 10.1055/s-2005-869973
PSP
© Georg Thieme Verlag Stuttgart · New York

Intramolecular Cyclopropanation of Epichlorohydrin-Derived Unsaturated Chlorohydrins

David M. Hodgson*a, Ying Kit Chunga, Jean-Marc Parisb
a Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
e-Mail: [email protected];
b Rhodia Recherches, Centre de Recherches de Lyon, 85 Avenue des Frères Perret, 69192 Saint Fons, France
Further Information

Publication History

Received 7 March 2005
Publication Date:
06 June 2005 (online)

Abstract

Concise stereoselective syntheses of bicyclo[3.1.0]hexan-2-ols and a bicyclo[4.1.0]heptan-2-ol are achieved via regioselective ring-opening of epichlorohydrin with allylic and homoallylic Grignard reagents, followed by lithium 2,2,6,6-tetramethylpiperidide-induced intramolecular cyclopropanation of the resulting unsaturated chlorohydrins.

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