Work

Rh(III)-Catalyzed Double C–H Activation toward Peptide–Benzazepine Conjugates

Year: 2024

Type: article

Abstract: 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c04498

Authors: Qi Quan, Yan Li, Zhefan Zhang, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song

Institutions: Nanjing Forestry University, Peoples' Friendship University of Russia, KU Leuven

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green