Regiocontrolled palladium-catalyzed and copper-mediated C-H bond functionalization of protected L-histidine.
We describe the controlled and regioselective transition-metal-catalyzed C-H bond arylation of protected L-histidine with aryl halides as the coupling partner. Using this approach, a large number of C-2 arylated L-histidines have been synthesized with diverse substitutions bearing electron-donating and electron-withdrawing groups, in good to excellent yields. These synthetic amino acids possessing dual hydrophobic-hydrophilic character are important synthons of bioactive peptidomimetics, which are imperative potent inhibitors of Cryptococcus neoformans.
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, S. A. S. Nagar, Punjab 160 062, India. rahuljain@niper.ac.in.
Amit
A
Mahindra
Rahul
R
Jain
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006639:Histidine / Q000737:chemistry*; D008024:Ligands; D008872:Microwaves; D010165:Palladium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D008024:Ligands; D012997:Solvents; D006639:Histidine; D010165:Palladium; D003300:Copper