Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol
作者： Caroline Aciro , Timothy D. W. Claridge , Stephen G. Davies , Paul M. Roberts , Angela J. Russell
DOI: 10.1039/B808811J
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摘要: Treatment of 3-aminocyclohex-1-enes with mCPBA in the presence trichloroacetic acid gives corresponding 1,2-anti-2,3-syn-1-trichloroacetoxy-2-hydroxy-3-aminocyclohexane high levels diastereoselectivity (90% de). This is consistent a mechanism oxidation involving hydrogen-bonded delivery oxidant by allylic ammonium ion formed situ, followed highly regioselective ring-opening intermediate epoxide acid. The effect conformational constraints upon reaction also examined.
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