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Issue 20, 2008
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Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol

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Abstract

Treatment of 3-aminocyclohex-1-enes with mCPBA in the presence of trichloroacetic acid gives the corresponding 1,2-anti-2,3-syn-1-trichloroacetoxy-2-hydroxy-3-aminocyclohexane with high levels of diastereoselectivity (90% de). This is consistent with a mechanism of oxidation involving hydrogen-bonded delivery of the oxidant by the allylic ammonium ion formed in situ, followed by highly regioselective ring-opening of the intermediate epoxide by trichloroacetic acid. The effect of conformational constraints upon the oxidation reaction is also examined.

Graphical abstract: Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol

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Publication details

The article was received on 27 May 2008, accepted on 29 Jul 2008 and first published on 20 Aug 2008


Article type: Paper
DOI: 10.1039/B808811J
Citation: Org. Biomol. Chem., 2008,6, 3751-3761
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    Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol

    C. Aciro, T. D. W. Claridge, S. G. Davies, P. M. Roberts, A. J. Russell and J. E. Thomson, Org. Biomol. Chem., 2008, 6, 3751
    DOI: 10.1039/B808811J

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