RT journal article
T1 Asymmetric microbial reduction of ketones: absolute configuration of trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol
A1 Pinedo Rivilla, Cristina
A1 Carrara Mafeu, Mariana
A1 Regina Araujo, Angela
A1 González Collado, Isidro
A1 Aleu Casatejada, Josefina
A2 Química Orgánica
K1 Asymmetric reduction,
K1 ketones
AB A set of five fungal species, Botrytis cinerea, Trichoderma viride and Eutypa lata, and the endophytic fungiColletotrichum crassipes and Xylaria sp., was used in screening for microbial biocatalysts to detect monooxygenaseand alcohol dehydrogenase activities (for the stereoselective reduction of carbonyl compounds).4-Ethylcyclohexanone and acetophenone were biotransformed by the fungal set. The mainreaction 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 was0:100. trans-4-Ethyl-1-(1S-hydroxyethyl)cyclohexanol, obtained from biotransformation by means ofan acyloin-type reaction, is reported here for the first time. The absolute configurations of the compoundstrans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol and 4-(1S- and 4-(1R-hydroxyethyl)cyclohexanone weredetermined by NMR analysis of the corresponding Mosher’s esters.
PB Elsevier
SN 0957-4166
YR 2009
FD 2009-11-26T00:00:00Z
LK http://hdl.handle.net/10498/17359
UL http://hdl.handle.net/10498/17359
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 21-sep-2026