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The substrate dependent competitive formation of cyclobutanones and cyclopentanones in an intramolecular rhodium carbenoid CH insertion reaction: enantiospecific total synthesis of silphiperfol-6-ene

Srikrishna, Adusumilli and Nagaraju, Gopalasetty (2012) The substrate dependent competitive formation of cyclobutanones and cyclopentanones in an intramolecular rhodium carbenoid CH insertion reaction: enantiospecific total synthesis of silphiperfol-6-ene. In: TETRAHEDRON-ASYMMETRY, 23 (2). pp. 170-175.

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Official URL: http://dx.doi.org/10.1016/j.tetasy.2012.01.016

Abstract

The enantiospecific total synthesis of silphiperfol-6-ene has been accomplished starting from the readily available monoterpene (R)-limonene, employing a rhodium carbenoid insertion into the CH bond of a tertiary methyl group. A substrate dependent competitive insertion of the rhodium carbenoid in the gamma- and beta-CH bonds to form cyclopentanone and cyclobutanones, respectively, has been described. (C) 2012 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to Elsevier
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 22 Jun 2012 12:01
Last Modified: 22 Jun 2012 12:03
URI: http://eprints.iisc.ernet.in/id/eprint/44554

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