Chemoenzymic resolution and deracemisation of (±)-1-methyl-1,2- epoxycyclohexane: The synthesis of (1-S, 2-S)-1-methylcyclohexane-1,2-diol

Ian V.J. Archer, David J. Leak, David A. Widdowson

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38 Citations (Scopus)

Abstract

Corynebacterium C12 epoxide hydrolase transforms (±)-1-methyl-1,2-epoxy-cyclohexane 1 to the (1-S, 2-S)-1-methylcyclohexane-1,2-diol 2 leaving the (1-S, 2-R)-epoxide 3 unchanged. The diol 2 is converted to the (1-R, 2-S)-epoxide 4 by sulfonation-ring closure. A one pot combination of Corynebacterium C12 epoxide hydrolase and acid catalysed ring opening converts (±)-1-methyl-1,2-epoxycyclohexane 1 to (1-S, 2-S)-1-methylcyclohexane-1,2-diol 2.

Original languageEnglish
Pages (from-to)8819-8822
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number48
DOIs
Publication statusPublished - 25 Nov 1996

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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