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.
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|
Actions (login required)