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.
Full text not available from this repository. (Request a copy)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 |
|---|---|
| Publication: | Journal of the Indian Chemical Society |
| Publisher: | Indian Chemical Society |
| 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.ac.in/id/eprint/38064 |
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