Synthesis 1992; 1992(1/2): 90-95
DOI: 10.1055/s-1992-34155
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Sabine Laschat* , Horst Kunz
  • *Institut für Organische Chemie, Universität Mainz, Becher-Weg 18-20, D-6500 Mainz, Germany
Further Information

Publication History

Publication Date:
18 September 2002 (online)

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.