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ChemInform Abstract Condensation of the chiral sulfoxides (I) with the esters (II) yields the poly-and monofluorocarbonyl compounds (III) possessing a chiral sulfinyl substituent ((IIIa) excists as a 65:35 mixture of the keto form and its hydrate; in the case of (IIIb) separable mixtures of diastereomers are obtained). The same reaction between (Ia) and the racemic ester (IV) leads to a diastereomeric 1:1 mixture of the ketones (V) and (VI); diastereoselection is achieved by preparing (V) and (VI) via alkylation of (VII).
ChemInform Abstract Removal of the chiral sulfinyl group of (I) leads to the title ketones (II). Stereoselective reduction of (III) yields the corresponding alcohols with >95% d.e., which undergo desulfination to give the title alcohols (IV) with pure anti stereochemistry.
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