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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.

Original publication

DOI

10.1039/b808811j

Type

Journal article

Journal

Org Biomol Chem

Publication Date

21/10/2008

Volume

6

Pages

3751 - 3761

Keywords

Amines, Cyclohexenes, Hydroxides, Hydroxylation, Metals, Molecular Conformation, Oxidation-Reduction, Quaternary Ammonium Compounds, Stereoisomerism, Substrate Specificity