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A new strategy for the alpha-vinylation of ketones: Application to an enantioselective synthesis of sesquiterpene (+)-alpha-elemene

Mehta, G and Acharyulu, PVR (1998) A new strategy for the alpha-vinylation of ketones: Application to an enantioselective synthesis of sesquiterpene (+)-alpha-elemene. In: Journal of the Indian Chemical Society, 75 (10-12). pp. 601-612.

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Official URL: http://www.indianchemicalsociety.org/

Abstract

A new, simple and preparatively useful protocol for the construction of a-vinyl ketones, particularly those bearing a quaternary carbon centre, from the corresponding alkenes has been devised. Our four-step strategy consists of dichloroketene addition, base catalysed ring contraction to 'push-pull' cyclopropane esters, reduction and eliminative cyclopropane fragmentation to unravel the a-vinyl ketone moiety. The generality of this approach has been demonstrated with a few representative olefins and good regio- and stereocontrol has been observed. As an application of this methodology, an enantioselective synthesis of sesquiterpene hydrocarbon (+)-alpha-elemene (42) from R-(+)-limonene (43) has been accomplished.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Indian Chemical Society.
Keywords: Stereocontrolled Synthesis;Dichloroketene;Construction; Cyclopropanes;Diterpenes;Framework;Terpenes;Route.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 10 Jun 2011 04:26
Last Modified: 10 Jun 2011 04:26
URI: http://eprints.iisc.ernet.in/id/eprint/38064

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