Stereochemical Control in Microbial Reduction. 8. Stereochemical Control in Microbial Reduction of β-Keto Esters

Article abstract of DOI:10.1246/bcsj.62.875

Stereochemistry of the reduction of β-keto esters with bakers' yeast is controlled by the addition of a certain α,β-unsaturated carbonyl compound (or its reduced form).Glucose also exerts the same effect.The additives tend to shift the stereochemistry of the reduction toward the production of D-hydroxy ester.Namely, methyl 3-oxopentanoate and ethyl 3-oxo-6-heptenoate were reduced to the corresponding D-hydroxy esters with excellent stereoselectivities and chemical yields.The enones are supposed to inhibit the enzymes that produce the L-hydroxy ester, whereas glucose plays a role to activate the enzymes that produce the D-hydroxy ester.