Asymmetric microbial reduction of ketones: absolute configuration of trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol

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URI: http://hdl.handle.net/10498/17359
DOI: 10.1016/j.tetasy.2009.11.001
ISSN: 0957-4166
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2009-11-26Department
Química OrgánicaSource
Tetrahedron: Asymmetry, 2009, vol. 20,pp. 2666–2672Abstract
A set of five fungal species, Botrytis cinerea, Trichoderma viride and Eutypa lata, and the endophytic fungi
Colletotrichum crassipes and Xylaria sp., was used in screening for microbial biocatalysts to detect monooxygenase
and alcohol dehydrogenase activities (for the stereoselective reduction of carbonyl compounds).
4-Ethylcyclohexanone and acetophenone were biotransformed by the fungal set. The main
reaction pathways involved reduction and hydroxylations at several positions including tertiary carbons.
B. cinerea was very effective in the bioreduction of both substrates leading to the chiral alcohol (S)-1-
phenylethanol in up to 90% enantiomeric excess, and the cis–trans ratio for 4-ethylcyclohexanol was
0:100. trans-4-Ethyl-1-(1S-hydroxyethyl)cyclohexanol, obtained from biotransformation by means of
an acyloin-type reaction, is reported here for the first time. The absolute configurations of the compounds
trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol and 4-(1S- and 4-(1R-hydroxyethyl)cyclohexanone were
determined by NMR analysis of the corresponding Mosher’s esters.
Subjects
Asymmetric reduction,; ketonesCollections
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