Stereoselective α‐Vinylation and α‐Arylation of a Racemic α-C-Tosyl Glycinyl Unit in a Peptide Backbone

Keywords

α‐vinylation - α‐arylation - α-C-tosyl glycinyl unit - cross-coupling - late-stage peptide backbone modification

Significance

The stereoselective modulation of peptide backbone α-carbons at internal sites was achieved. The authors developed stereoselective α‐vinylation and α‐arylation of the racemic α-C-tosyl glycinyl unit via Ni/chiral BiIm-catalyzed asymmetric reductive coupling.

Comment

Various α-C(sp²)-modified peptides were prepared with high diastereoselectivity through α‐vinylation and α‐arylation of a racemic α-C-tosyl glycinyl unit in peptide backbones. This protocol provides novel methods for late-stage structural diversification of peptides and voids racemization issues encountered in conventional peptide synthesis.

Publikationsverlauf

Artikel online veröffentlicht:
16. Dezember 2025