Abstract

Stereoselective synthesis of (5 R,6 R)- and (5 S,6 S)-5-benzylamino-6-( tert-butyldimethylsilanyloxymethyl)-5,6-dihydropyran-2-ones starting from d-glucal and furanaldehyde, respectively, is described. The synthesis relies on a Sharpless asymmetric dihydroxylation, an Achmatowicz reaction, and a stereoselective Pd-catalyzed allylic amination as the key steps.

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