Free Amino Group Transfer via α-Amination of Native Carbonyls

Abstract

We report herein a straightforward transfer of a free amino group (NH₂ ) from a commercially available nitrogen source to unfunctionalized, native carbonyls (amides and ketones) resulting in direct α-amination. Primary α-amino carbonyls are readily produced under mild conditions, further enabling diverse in situ functionalization reactions-including peptide coupling and Pictet-Spengler cyclization-that capitalize on the presence of the unprotected primary amine.

Keywords: Peptides; Primary Amine; Sulfonium [2,3]-Rearrangement; α-Amino Carbonyls.