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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.

SUBMITTER: Feng M

PROVIDER: S-EPMC10952782 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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Free Amino Group Transfer via α-Amination of Native Carbonyls.

Feng Minghao M Fernandes Anthony J AJ Sirvent Ana A Spinozzi Eleonora E Shaaban Saad S Maulide Nuno N

Angewandte Chemie (International ed. in English) 20230605 28

We report herein a straightforward transfer of a free amino group (NH<sub>2</sub> ) 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. ...[more]

PMID: 37114555

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