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The direct preparation of functionalised cyclopropanes from allylic alcohols or a-hydroxyketones using tandem oxidation processes

McAllister, G.D., Oswald, M.F., Paxton, P.J., Raw, S.A. and Taylor, R.J.K. (2006) The direct preparation of functionalised cyclopropanes from allylic alcohols or a-hydroxyketones using tandem oxidation processes. Tetrahedron, 62 (12). pp. 6681-6694. ISSN 0040-4020

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Abstract

New manganese dioxide-mediated tandem oxidation processes (TOPs) have been developed, which facilitate the direct conversion of allylic alcohols and α-hydroxyketones into polysubstituted functionalised cyclopropanes. In the simplest version, the oxidation of an allylic alcohol is carried out in the presence of a stabilised sulfurane, and the intermediate α,β-unsaturated carbonyl compound undergoes in situ cyclopropanation. By using a combination of stabilised phosphorane and sulfurane, the direct conversion of allylic alcohols or α-hydroxyketones into functionalised cyclopropanes is achieved, with in situ cyclopropanation being followed by Wittig olefination, or vice versa. The application of these methods to a formal synthesis of the lignan (±)-picropodophyllone, and to novel analogues of the insecticide allethrin II, is described.

Item Type: Article
Academic Units: The University of York > Chemistry (York)
Depositing User: York RAE Import
Date Deposited: 04 Mar 2009 16:55
Last Modified: 04 Mar 2009 16:55
Published Version: http://dx.doi.org/10.1016/j.tet.2005.12.078
Status: Published
Publisher: Elsevier Science B.V., Amsterdam.
Identification Number: 10.1016/j.tet.2005.12.078
URI: http://eprints.whiterose.ac.uk/id/eprint/7585

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