TY - JOUR
AU - Fessner, Wolf‐Dieter
AB - 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 °C 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 α‐amino acids in small‐ to large‐scale quantities.
TI - One‐Pot, Regioselective Synthesis of Substituted Arylglycines for Kinetic Resolution by Penicillin G Acylase
JO - Advanced Synthesis & Catalysis
DO - 10.1002/adsc.200800203
DA - 2008-08-04
UR - https://www.deepdyve.com/lp/wiley/one-pot-regioselective-synthesis-of-substituted-arylglycines-for-YUh5tN07PX
SP - 1729
EP - 1735
VL - 350
IS - 11‐12
DP - DeepDyve
ER -