The rabbit liver microsomal P-450 catalyzed oxidation of styrene (1a) and isomeric phenylpropenes, trans-1-phenylpropene (1b), cis-1-phenylpropene (1c) and 3-phenylpropene (1d), was investigated and the enantioselectivity of the epoxidation of the olefinic double bond was determined by checking the enantiomeric excesses of the corresponding first formed epoxides (2). These enantiomeric excesses were always modest, ranging 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.
ENANTIOSELECTIVITY IN THE RABBIT LIVER MICROSOMAL BIOTRANSFORMATION OF STYRENE AND PHENYLPROPENES
CHIAPPE, CINZIA;
1994-01-01
Abstract
The rabbit liver microsomal P-450 catalyzed oxidation of styrene (1a) and isomeric phenylpropenes, trans-1-phenylpropene (1b), cis-1-phenylpropene (1c) and 3-phenylpropene (1d), was investigated and the enantioselectivity of the epoxidation of the olefinic double bond was determined by checking the enantiomeric excesses of the corresponding first formed epoxides (2). These enantiomeric excesses were always modest, ranging 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.