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

All articles of this category 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.