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.
1994
Bellucci, G; Chiappe, Cinzia; Cordoni, A; Marioni, F.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/22838
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