Abstract
Abstract 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.
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