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Synthesis of Enantiomerically Enriched Alkynylaryl‐Substituted α‐Amino Acids through Sonogashira Reactions
Author(s) -
Saghyan Ashot S.,
Mkrtchyan Anna F.,
Mardiyan Zorayr Z.,
Hayriyan Liana A.,
Karapetyan Ani J.,
Belokon Yuri N.,
Ehlers Peter,
Langer Peter
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903072
Subject(s) - sonogashira coupling , moiety , chemistry , amino acid , enantiomer , aryl , benzophenone , hydrolysis , enantiomeric excess , aqueous solution , bromide , organic chemistry , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , palladium , catalysis , biochemistry , alkyl
Abstract Various enantiomerically enriched non‐proteinogenic ( S )‐α‐amino acids were obtained in high chemical and optical yields through Sonogashira cross‐coupling reactions and Glaser couplings. The Schiff base Ni(II)complexes of the chiral auxiliary ( S )‐BPB (BPB=N‐benzyl proline benzophenone) and an amino acid containing an aryl bromide moiety in the α‐position were synthesized and subsequently used in Sonogashira coupling reactions. The obtained Ni(II) complexes were hydrolyzed with aqueous HCl and novel amino acids, containing an alkynylaryl moiety, were isolated in good yields and with high enantiomeric excess (>99% ee ). The chiral auxiliary ( S )‐BPB can be recycled and reused for the synthesis of the starting Ni(II) complex.