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Synthesis of Enantiomerically Enriched Non‐Proteinogenic α‐Amino Acids Using the Suzuki Reaction
Author(s) -
Saghyan Ashot S.,
Mkrtchyan Anna F.,
Mardiyan Zorayr Z.,
Hayriyan Liana A.,
Belokon Yuri N.,
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.201900698
Subject(s) - synthon , chemistry , benzophenone , amino acid , moiety , phenylalanine , ligand (biochemistry) , carbon fibers , side chain , schiff base , enantioselective synthesis , aqueous solution , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , materials science , biochemistry , receptor , composite number , composite material , polymer
Herein we report the synthesis of a variety of new enantiomerically enriched non‐protein ( S )‐α‐amino acids based on the reaction of generating new carbon‐carbon bonds in the side chain group of the amino acid moiety with high chemical yields and optical purity using the reaction of Suzuki. As the initial synthon, the Schiff base Ni(II) complex of the chiral auxiliary ( S )‐BPB (N‐benzyl proline benzophenone) and 4‐bromo‐ L ‐phenylalanine amino acid was used. The final Ni(II) complexes were decomposed with aqueous HCl and the amino acids were isolated with excellent enantioselectivities (>99% ee). The chiral auxiliary ligand ( S )‐BPB can be recycled and reused for the synthesis of starting Ni(II) complex.