TY - JOUR
T1 - Chemoenzymic resolution and deracemisation of (±)-1-methyl-1,2- epoxycyclohexane
T2 - The synthesis of (1-S, 2-S)-1-methylcyclohexane-1,2-diol
AU - Archer, Ian V.J.
AU - Leak, David J.
AU - Widdowson, David A.
PY - 1996/11/25
Y1 - 1996/11/25
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=16144362981&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(96)01998-3
DO - 10.1016/S0040-4039(96)01998-3
M3 - Article
AN - SCOPUS:16144362981
SN - 0040-4039
VL - 37
SP - 8819
EP - 8822
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 48
ER -