Palladium‐Catalyzed Site‐Selective C(sp<sup>2</sup>)−H Acetoxylation of Tyrosine‐Containing Peptides
Iñaki Urruzuno, Paula Andrade‐Sampedro, Arkaitz Correa
Abstract
Abstract A Pd‐catalyzed C(sp 2 )−H acetoxylation of Tyr‐containing peptides is described. The method relies on the use of a removable 2‐pyridyloxy group as directing group and is distinguished by its reliable scalability and easily tuned regioselectivity to perform mono‐ and diacetoxylation reactions. Remarkably, the assembly of L–DOPA peptidomimetics is beyond reach upon cleavage of the directing group.
Topics & Concepts
ChemistryPalladiumRegioselectivityPeptidomimeticCatalysisStereochemistryCleavage (geology)TyrosineCombinatorial chemistryPeptideMedicinal chemistryOrganic chemistryBiochemistryGeotechnical engineeringEngineeringFracture (geology)Catalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions