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

doi:10.1016/S0040-4039(96)01998-3

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

Imperial College London

Research output: Contribution to journal › Article › peer-review

39 Citations (SciVal)

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 language	English
Pages (from-to)	8819-8822
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(96)01998-3
Publication status	Published - 25 Nov 1996

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(96)01998-3

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

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.",

author = "Archer, \{Ian V.J.\} and Leak, \{David J.\} and Widdowson, \{David A.\}",

year = "1996",

month = nov,

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doi = "10.1016/S0040-4039(96)01998-3",

language = "English",

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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 - https://www.scopus.com/pages/publications/16144362981

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 -

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

Abstract

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