Carbohydrates as Chiral Templates: Stereoselective Synthesis of (R)- and (S)-α-Aminophosphonic Acid Derivatives

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Abstract
The stereoselective synthesis of diethyl (S)- or (R)-α-[(O-pivaloyl-hexapyranosyl) amino]benzylphosphonates is achieved via Lewis acid catalyzed addition of diethyl phosphite to O-pivaloylated N-benzylidene -β-D-galactosylamine or N-benzylidene-α-D-arabinopyranosylamine. The process can also be performed by a one-pot procedure selectively giving (S)-aminophosphonic acid derivatives from galactosylamine and (R)-aminophosphonic acid derivatives from β-L-fucosylamine as the chiral auxiliaries.