σ-Ferrier rearrangement of carbohydrate derived vinylcyclopropanes: a facile approach to oxepane analogs |
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Authors: | Venkataraman Ganesh Taraknath Kundu Srinivasan Chandrasekaran |
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Institution: | 1. Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India;2. JNCASR, Jakkur, Bangalore, India |
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Abstract: | This article presents our work on the σ-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. |
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Keywords: | Carbohydrate Vinylcyclopropane σ-Ferrier rearrangement Oxepane Septanoside Heptanoside |
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