Asymmetric synthesis of β-amino acid derivatives by stereocontrolled C(sp³)-C(sp²) cross-electrophile coupling via radical 1,2-nitrogen migration.

ABSTRACT: Optically pure non-natural β-amino acids are noteworthy molecular motifs of numerous pharmaceutically important molecules. Skeletal editing of abundant α-amino acid scaffolds via tandem radical 1,2-N-shift/cross-coupling represents a powerful tool to straightforward assemble new β-amino acid molecules; however, this strategy presents substantial challenges owing to difficulties in reactivity and regio-/enantiocontrol. Herein, we report a cross-electrophile C(sp²)-C(sp³) coupling of β-bromo α-amino acid esters with aryl bromides via a π-system-independent 1,2-N-shift, which allows access to α-arylated β-amino acid motifs with high efficiency and regioselectivity. Furthermore, upon the cooperative catalysis of the Ni(II)/ cyclo-Box complex and chiral phosphoric acid, th

SUBMITTER: Liao Z 

PROVIDER: S-EPMC12325796 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature