ENANTIOSELECTIVITY IN THE RABBIT LIVER MICROSOMAL BIOTRANSFORMATION OF STYRENE AND PHENYLPROPENES

The rabbit liver microsomal P-450 catalyzed oxidation of styrene (1a) and isomeric phenylpropenes, trans-1-phenylpropene (1b), cis-1-phenylp ropene (1c) and 3-phenylpropene (1d), was investigated and the enantio selectivity of the epoxidation of the olefinic double bond was determi ned by checking the enantiomeric excesses of the corresponding first f ormed epoxides (2). These enantiomeric excesses were always modest, ra nging between 7% of (1S,2S)-(2b) and 22% of (1R,2R)-(2c). In the case of (1d) a non-enantioselective hydroxylation at the benzylic-allylic C (3) was also observed. The ratio between this hydroxylation and olefin epoxidation of (1d) was 1:2.