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Asymmetric Synthesis of β 2 ‐Aryl Amino Acids through Pd‐Catalyzed Enantiospecific and Regioselective Ring‐Opening Suzuki–Miyaura Arylation of Aziridine‐2‐carboxylates
Author(s) -
Takeda Youhei,
Matsuno Tetsuya,
Sharma Akhilesh K.,
Sameera W. M. C.,
Minakata Satoshi
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902009
Subject(s) - aziridine , regioselectivity , enantiopure drug , chemistry , aryl , ring (chemistry) , catalysis , enantioselective synthesis , serine , amino acid , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , alkyl , enzyme
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 β 2 ‐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.