A Gold‐Catalyzed Acid‐Assisted Regioselective Cyclization for the Synthesis of Polysubstituted Oxazoles
Qian Wang, Stephanie Hoffmann, Jasmin Schießl, Matthias Rudolph, Frank Röminger, A. Stephen K. Hashmi
Abstract
Polysubstituted oxazole derivatives are obtained through a regioselective gold‐catalyzed reaction of α‐alkynylamides and alkynoates in the presence of nitriles. The intermediary obtained gold carbenes are generated by alkyne oxidation with a pyridine N ‐oxide. Acidic conditions ensure that only one of the two carbonyl oxygen atoms in these intermediates selectively cyclizes to the products in excellent yields.
Topics & Concepts
RegioselectivityChemistryOxazoleAlkyneCatalysisPyridineCombinatorial chemistryOrganic chemistryCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods