Photocatalytic Synthesis of Difluorinated Glycoamino Acids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides
A photocatalytic approach for the synthesis of difluorinated glycoamino acids and neoglycopeptides from bromodifluoroacetamides and sugar-derived olefins is presented. This method stands out because of its simplicity, atomic economy, and mild reaction conditions, allowing compatibility with both natural and unnatural amino acids and peptides. Additionally, it demonstrates efficacy across a variety of carbohydrates, including furanoses, pyranoses, pentose, hexoses, and disaccharides, accommodating an extensive range of protecting groups, even in their deprotected forms.
Authors
- Márcio W. Paixão (ORCID: https://orcid.org/0000-0002-0421-2831)
- Emanuele F. Pissinati (ORCID: https://orcid.org/0000-0002-5892-8528)
- Till Opatz (ORCID: https://orcid.org/0000-0002-3266-4050)
- Lívia M. S. Barreto
Institutions
- Universidade Federal de São Carlos (BR)
- Johannes Gutenberg University Mainz (DE)
- Laboratoire de Synthèse Organique (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-03-04
- DOI
- https://doi.org/10.1021/acs.joc.5c00030
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.37
Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico