Free Amino Group Transfer via a-Amination of Native Carbonyls

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 a-amination. Primary a-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.

Automated summary

We present a simple method for the direct amination of unfunctionalized, native carbonyls (amides and ketones) by transferring a free amino group (NH2) from a commercially available nitrogen source. Mild conditions enable the production of primary a-amino carbonyls, allowing for diverse in situ functionalization reactions, such as peptide coupling and Pictet-Spengler cyclization, that take advantage of the presence of the unprotected primary amine.