Synthesis of chiral benzyl alkyl sulfoxides by cyclohexanone Monooxygenase from Acinetobacter NCIB 9871

Benzylalkyl sulfides with alkyl groups from methyl to hexyl, para-alkylbenzyl groups from methyl to butyl, 2-phenylethyl methyl sulfide and 3-phenylpropyl methyl sulfide have been oxidized by cyclohexanonemonooxygenase from AcinetobacterNCIB9871. Sulfoxides with enantiomeric excesses ranging from 80% for the (R)-configuration to 96% ee for the (S)-configuration were obtained. Cyclohexanonemonooxygenase (CMO) catalyzed the asymmetric oxidation of numerous benzylalkyl sulfides to sulfoxides with ee up to 96%.