ASYMMETRIC EPOXIDATION OF ALLYL ALCOHOL DERIVATIVES BY OMEGA-HYDROXYLASE FROM PSEUDOMONAS-OLEOVORANS

This paper described the application of non-heme monooxygenase system from Pseudomonas oleovorans to the syntheses of chiral 3-(benzyloxy)-, 3-(allyloxy)-, 3-(butyloxy)- and 3-(aryloxy)-1,2-epoxypropanes (6) from their corresponding allyl alcohol derivatives. The epoxides were determined to be R forms with good enantiomeric excess. The specificities of the enzymatic epoxidation of olefines and hydroxylation of the radical probe trans-2-phenyl-1-methylcyclopropane were discussed with regard to the reaction mechanism.