Synthetic amino acids are of interest in various fields of chemistry, biochemistry and pharmacy. The first experiments with a phosphanyl group were obtained by condensation of natural amino acids with secondary phosphanes and formaldehyde, usually forming bis(phosphanylmethyl) amino acids, and studied with respect to their use as ligands in rhodium-catalysed hydrogenation reactions and in complexes for radio-diagnostics. The use of primary phosphanes extended the range of N-phosphanylmethyl amino acids to various P,N-heterocyclic types. The incorporation of P-alkyl instead of Pphenyl groups led to an increase in the sensitivity of Nalkyl-α-phosphanylglycines. To obtain more stable α-phosphanyl amino acids we systematically varied the nitrogen substituents of the (diphenylphosphanyl)glycines and report here on the novel N-aryl derivatives 1, their synthesis, structure and properties, and the first examples of their transitionmetal complexes and their use in homogeneous catalysis.
A three-component one-pot reaction of diphenylphosphine, primary amine and glyoxylic acid hydrate in diethyl ether or methanol allowed an easy access to N-monosubstituted diphenylphosphinoglycines 1b-10b.