Journal of Organic Chemistry 2001-01-01

Asymmetric Synthesis of alpha-Amino Phosphonic Acids by Diastereoselective Addition of Trimethyl Phosphite onto Chiral Oxazolidines(1).

Catherine Maury, Tawfik Gharbaoui, Jacques Royer, Henri-Philippe Husson

Index: J. Org. Chem. 61 , 3687, (1996)

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Abstract

A simple and general asymmetric synthesis of alpha-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-alpha-substituted amino phosphonic acids in good overall yields and high ee (77-->97%) after simple deprotection.