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Biocatalytically derived enantiopure α‐substituted β‐hydroxy esters serve as excellent chirons for the synthesis of a diverse set of structures such as oxetanes, a carbohydrate mimic, an ϵ‐lactone, and carbocyclic and aromatic cyclitols. The starting materials can be easily accessed in enantiopure form from α‐substituted β‐keto esters by biocatalytic reduction with Klebsiella pneumoniae (NBRC 3319). Ring‐closing metathesis (RCM) is one of the key transformations used to create the carbocyclic/heterocyclic frameworks reported in this article. The synthesized cyclitols were screened for their inhibitory effect on α‐ and β‐glucosidases.

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Ketoreductase from growing cells of Klebsiella pneumoniae (NBRC 3319) acts as an efficient reagent for converting racemic α-benzyl/cinnamyl substituted-β-ketoesters to the corresponding β-hydroxy esters with excellent yields and stereoselectivities (ee and de >99%).