A³-Mannich coupling reaction <i>via</i> chiral propargylglycine Ni(ii) complex: an approach for synthesizing enantiomerically enriched unnatural α-amino acids.

ABSTRACT: A novel hybrid synthetic approach was developed for the enantioselective synthesis of unnatural α-amino acids, utilizing chiral square-planar Ni(ii) Schiff base complexes in combination with an A³-coupling (Mannich-type) reaction. The methodology enabled the generation of a series of α-amino acid derivatives with excellent enantiomeric excess (≥99% ee) and high chemical yields under optimized reaction conditions involving CuI/FeCl₃ catalysis in toluene under argon. The reaction demonstrated strong dependence on the nature of the amine, with cyclic secondary amines yielding superior results compared to linear or primary analogs. The obtained products were structurally confirmed via X-ray crystallography and HPLC analysis, verifying the retention of stereochemica

SUBMITTER: Hayriyan L 

PROVIDER: S-EPMC12461245 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature