Carbohydrates as chiral templates : stereoselective synthesis of (R)- and (S)-α-aminophosphonic acid derivatives

Laschat, SabineKunz, Horst2009-07-212016-03-312009-07-212016-03-311992314608877http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-41688http://elib.uni-stuttgart.de/handle/11682/7003http://dx.doi.org/10.18419/opus-6986The 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.eninfo:eu-repo/semantics/openAccessKohlenhydrate , Stereoselektive Synthese , Aminophosphonsäurederivate540Carbohydrates as chiral templates : stereoselective synthesis of (R)- and (S)-α-aminophosphonic acid derivativesarticle2013-06-12