Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol

Org Biomol Chem. 2008 Oct 21;6(20):3762-70. doi: 10.1039/b808812h. Epub 2008 Aug 20.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclohexanols / chemical synthesis*
  • Cyclohexanols / chemistry
  • Cyclohexylamines / chemical synthesis*
  • Cyclohexylamines / chemistry
  • Hydroxides / chemistry*
  • Hydroxylation
  • Metals / chemistry
  • Oxidation-Reduction
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • 3-aminocyclohexane-1,2-diol
  • Cyclohexanols
  • Cyclohexylamines
  • Hydroxides
  • Metals
  • Quaternary Ammonium Compounds
  • hydroxide ion