Highly enantioselective kinetic resolution of trans-2-(phenylthio)cyclohexanol derivatives by immobilized Candida antartica B lipase

• Candida antartica B lipase catalyzed highly enantioselective resolution of trans-2-(phenylthio)cyclohexanol.
• Methyl tert-butyl ether provides an efficient medium for kinetic resolution.
• The resolved hydroxy sulfides upon oxidation provide a very convenient method for obtaining chiral hydroxy sulfoxides which are otherwise difficult to obtain by traditional methods.
• The configuration to the stereogenic centers assigned on the basis of single crystal X-ray analysis.

Candida antartica B (immobilized CAL-B) mediated resolutions of trans-2-(phenylthio)cyclohexanol derivatives using vinyl acetate as acylating agent and MTBE as solvent provide excellent enantioselectivity (up to >99%) and high yield of both the enantiomers in short reaction time.

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