Rh(III)-Catalyzed Double C–H Activation toward Peptide–Benzazepine Conjugates
We herein report the efficient synthesis of peptide-benzazepine conjugates from Lys-based peptides and acroleins via Rh(III)-catalyzed double C-H activation. This reaction features mild reaction conditions, broad scope, high atom and step economies, and excellent chemo- and site selectivity. The synthetic utility of this strategy is further demonstrated by scale-up experiments and product derivatizations, including diverse late-stage ligations based on the aldehyde moiety. The preliminary biological activity studies show that peptide-benzazepine conjugates have good antifungal activities toward crop and forest pathogenic fungi.
Authors
- Yan Li (ORCID: https://orcid.org/0000-0002-0771-1425)
- Zhefan Zhang
- Erik V. Van der Eycken (ORCID: https://orcid.org/0000-0001-5172-7208)
- Liangliang Song (ORCID: https://orcid.org/0000-0003-1934-5132)
- Lingchao Cai (ORCID: https://orcid.org/0000-0001-9038-2724)
- Qi Quan
Institutions
- Peoples' Friendship University of Russia (RU)
- Nanjing Forestry University (CN)
- KU Leuven (BE)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-23
- DOI
- https://doi.org/10.1021/acs.orglett.4c04498
- Citations
- 4
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- Government of Jiangsu Province
- Fonds Wetenschappelijk Onderzoek
- KU Leuven
- Natural Science Foundation of Jiangsu Province
- Vlaamse regering
- RUDN University