Carbohydrates as Chiral Templates : Stereoselective Synthesis of ( R ) - and ( S ) - ~ - Aminophosphonic Acid Derivatives
نویسندگان
چکیده
The stereoselective synthesis of diethyl (S)or (R)-IX-[( O-pivaloylhexapyranosyl)amino]benzylphosphonates is achieved via Lewis acid catalyzed addition of diethyl phosphite to O-pivaloylated Nbenzylidene-{3-D-galactosylamine or N-benzylidene-IX-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 {3-L-fucosylamine as the chiral auxiliaries.
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