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A reagent-controlled, diastereo- and enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates has been achieved by the proper choice of solvent, temperature, alkoxy group, and amine for the diisopinocampheylboron-mediated asymmetric enolization–aldolization of phenylacetates. The pure diastereomers can be readily separated by column chromatography.
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