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

✍ Scribed by Ian V.J. Archer; David J. Leak; David A. Widdowson

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
170 KB
Volume
37
Category
Article
ISSN
0040-4039

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✦ Synopsis

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

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