Asymmetric Synthesis of β2 -Aryl Amino Acids through Pd-Catalyzed Enantiospecific and Regioselective Ring-Opening Suzuki-Miyaura Arylation of Aziridine-2-carboxylates

Abstract

A Pd-catalyzed enantiospecific and regioselective ring-opening Suzuki-Miyaura arylation of aziridine-2-carboxylates was developed. The cross-coupling allows for the asymmetric preparation of enantioenriched β² -aryl amino acids, starting from commercially available enantiopure d- and l-serine esters. The mechanism and selectivity of the reaction was rationalized based on computational models.

Keywords: amino acids; asymmetric synthesis; cross-coupling; nitrogen heterocycles; regioselectivity.