Asymmetric Synthesis of β2 -Aryl Amino Acids through Pd-Catalyzed Enantiospecific and Regioselective Ring-Opening Suzuki-Miyaura Arylation of Aziridine-2-carboxylates.
Youhei TakedaTetsuya MatsunoAkhilesh K SharmaW M Chamil SameeraSatoshi MinakataPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2019)
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.