Microbial hydroxylation of unsaturated, cyclic carboxylic acids protected as benzoxazoles |
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| Authors: | A. de Raadt S. Feichtenhofer H. Griengl M. F. Klingler H. Weber |
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| Affiliation: | Institute of Organic Chemistry, SFB F001 Biokatalyse Technical University Graz, Stremayrgasse 16, A-8010 Graz, Austria |
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| Abstract: | Microbial hydroxylation of 2-(cyclopent-1-enyl)benzoxazole (1) and 2-(cyclohex-1-enyl)benzoxazole (2) by Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32, respectively, gave chiral allylic alcohols 3-(benz-1,3-oxazol-2-yl)cyclopent-2-en-1-ol (3) and 3-(benz-1,3-oxazol-2-yl)cyclohex-2-en-1-ol (4) along with achiral ketones 3-(benz-1,3-oxazol-2-yl)cyclopent-2-en-1-one (5) and 3-(benz-1,3-oxazol-2-yl)cyclohex-2-en-1-one (6). Both allylic alcohols were produced in enantiomeric excesses higher than 99%. The determination of their absolute configurations (S in both cases) is described. |
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| Keywords: | Microbial hydroxylation Benzoxazoles Cunninghamella blakesleeana Bacillus megaterium Stereochemistry |
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