CHEMOENZYMIC RESOLUTION AND DERACEMISATION OF (+ -)-1-METHYL-1,2-EPOXYCYCLOHEXANE - THE SYNTHESIS OF(1-S,2-S)-1-METHYLCYCLOHEXANE-1,2-DIOL/

Authors
ARCHER IVJ LEAK DJ WIDDOWSON DA
Citation
Ivj. Archer et al., CHEMOENZYMIC RESOLUTION AND DERACEMISATION OF (+ -)-1-METHYL-1,2-EPOXYCYCLOHEXANE - THE SYNTHESIS OF(1-S,2-S)-1-METHYLCYCLOHEXANE-1,2-DIOL/, Tetrahedron letters, 37(48), 1996, pp. 8819-8822
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
48
Year of publication
1996
Pages
8819 - 8822
Database
ISI
SICI code
0040-4039(1996)37:48<8819:CRADO(>2.0.ZU;2-J
Abstract
Corynebacterium C12 epoxide hydrolase transforms (+/-)-1-methyl-1,2-ep oxy-cyclohexane 1 to the (1-S, 2-S)-1-methylcyclohexane-1,2-diol 2 lea ving the (1-S, 2-R)-epoxide 3 unchanged. The diol 2 is converted to th e the (1-R, 2-S)-epoxide 4 by sulfonation-ring closure. A one pot comb ination of Corynebacterium C12 epoxide hydrolase and acid catalysed ri ng opening converts (+)-1-methyl-1,2- epoxycyclohexane 1 to (1-S, 2-S) -1-methylcyclohexane-1,2-diol 2. Copyright (C) 1996 Elsevier Science L td