McAllister, G.D., Oswald, M.F., Paxton, P.J. et al. (2 more authors) (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
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (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 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:7585 |