Intramolecular Cyclopropanation of Unsaturated Terminal Epoxides

David M. Hodgson,* Ying Kit Chung and Jean-Marc Paris

*Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, U.K., Email: david.hodgsonchem.ox.ac.uk

D. M. Hodgson, Y. K. Chung, J.-M. Paris, J. Am. Chem. Soc., 2004, 126, 8664-8665.

DOI: 10.1021/ja047346k

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Abstract

An efficient lithium amide-induced intramolecular cyclopropanation of bishomoallylic and trishomoallylic epoxides is described. The methodology is used in an asymmetric synthesis of sabina ketone.

see article for more examples

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Intramolecular Cyclopropanation of Unsaturated Terminal Epoxides and Chlorohydrins

D. M. Hodgson, Y. K. Chung, I. Nuzzo, G. Freixas, K. K. Kulikiewicz, E. Cleator, J.-M. Paris, J. Am. Chem. Soc., 2007, 126, ASAP.

DOI: 10.1021/ja0672932

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Key Words

Cyclopropanes, Cyclopentanols, Cyclohexanols

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ID: J48-Y2004-1590