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The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

Original publication

DOI

10.1039/b808812h

Type

Journal article

Journal

Org Biomol Chem

Publication Date

21/10/2008

Volume

6

Pages

3762 - 3770

Keywords

Cyclohexanols, Cyclohexylamines, Hydroxides, Hydroxylation, Metals, Oxidation-Reduction, Quaternary Ammonium Compounds, Stereoisomerism, Substrate Specificity