Enantioselective synthesis of ?-aminophosphonic acid derivatives by hydrogenation

Abstract

Chiral α-aminophosphonic acid derivatives are efficiently synthesized by asymmetric hydrogenation of the prochiral N-acyl-α,β-dehydroaminophosphonates. PROPRAPHOS-Rh-catalysts from readily available (S)- and (R)-Propranolol proved to be suitable in the homogenous reaction affording an enantiomeric excess of 87–92% with high rate. The aminophosphonic acid derivatives and precursors were fully characterized by 1H, 13C, and 31P NMR spectroscopy. Chirality 10:564–572, 1998. © 1998 Wiley-Liss, Inc.