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sigma-Ferrier rearrangement of carbohydrate derived vinylcyclopropanes: a facile approach to oxepane analogs

Ganesh, Venkataraman and Kundu, Taraknath and Chandrasekaran, Srinivasan (2014) sigma-Ferrier rearrangement of carbohydrate derived vinylcyclopropanes: a facile approach to oxepane analogs. In: TETRAHEDRON, 70 (40, SI). pp. 7268-7282.

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Official URL: http://dx.doi.org/ 10.1016/j.tet.2014.07.004

Abstract

This article presents our work on the sigma-Ferrier ring-expansion of carbohydrate derived vinylcyclopropanes (VCPs) under electrophilic conditions mediated by chloramine-T and a phase-transfer catalyst. The present work serves as the first example on the studies of the reactivity of carbohydrate VCPs towards the synthesis of densely functionalized oxepane analogues. The work elaborates on a reasonable mechanism for the product formation and our observations on the diastereoselectivity based on control experiments and gas-phase calculations. (C) 2014 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Keywords: Carbohydrate; Vinylcyclopropane; sigma-Ferrier rearrangement; Oxepane; Septanoside; Heptanoside
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 12 Nov 2014 05:12
Last Modified: 12 Nov 2014 05:12
URI: http://eprints.iisc.ac.in/id/eprint/50221

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