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Stereoselective synthesis, solution structure and metal complexes of (1S,2S)-2-amino-1-hydroxyalkylphosphonic acids

✍ Scribed by Marcin Drag; Rafal Latajka; Elzbieta Gumienna-Kontecka; Henryk Kozlowski; Pawel Kafarski

Book ID: 104359829
Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 316 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00278-7

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✦ Synopsis

The highly stereoselective synthesis of (1S,2S)-2-amino-1-hydroxyalkylphosphonic acids was achieved by addition of dimethyl phosphite to N-protected aminoaldehydes. Relative configuration and solution conformations of (1S,2S)-2-amino-1hydroxy-alkylphosphonic acids (in D 2 O) and their dimethyl esters (in CDCl 3 and CD 3 OD) were established by means of NMR basing on the dependence between observed values of coupling constants ( 3 J HH , 3 J PC , 3 J HP ) and corresponding dihedral angles. Potentiometric and spectroscopic methods were used for the evaluation of the structure of the complexes of (1S,2S)-2-amino-1hydroxy-alkylphosphonic acids with Zn(II) and Cu(II) ions in aqueous solutions.

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