A comparison of the enantioselective reduction potential of five strains of Saccharomyces cerevisiae towards a selected ketone

The enantioselectivity potential of five strains of Saccharomyces cerevisia e was studied for the reduction of ethyl N-{2-{4-[(2-oxocyclohexyl)methyl]p henoxy}ethyl} carbamate (1), an insect juvenile hormone bioanalog. The prod ucts of the reaction, the cis and trans isomers of ethyl N-{2-{4-[(2-hydrox ycyclohexyl)methyl]phenoxy}ethyl} carbamate (2 and 3), were obtained in 45- 49% (w/w) chemical yields and with 79 to > 99% enantiomeric purity values. The absolute configurations of the major products were assigned as ethyl (1 S,2S)-N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl} carbamate (2) and ethyl (1S,2R)-N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl} carbamat e (3). The products 2 and 3 belong to the series of the chiral insect juven ile hormone analogs.