Amido-alkylation of electron-rich arenes with phenylacetamide and glyoxylic acid offers an inexpensive route to a large variety of N-phenylacetylated arylglycines that are suited for immediate enzymatic resolution by penicillin G acylase. When performed under mild conditions at 5 8C in acetic acid/ HCl, this simple one-pot operation resulted in the formation of single regioisomers only (! 98%). Subsequent kinetic resolution of the amino acid derivatives by penicillin G acylase at pH 8.0 occurred generally with E values > 100 and thus furnished free (S)-configurated arylglycines with high enantiomeric purity. The corresponding enantiopure (R)-substrates, easily separable by a phase-selective extraction process, provided the corresponding (R)-enantiomers upon conventional hydrolysis. This one-pot, two-step procedure for arylglycine synthesis, resolution and work-up requires a minimum of equipment and grants rapid access to both enantiopure (S)-and (R)-antipodes of non-natural a-amino acids in smallto large-scale quantities.
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