Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)<sub>2</sub>-Catalyzed Reactions of Ynamides with <i>t</i>-Butyl Carbamates/Carbonates
Pan Han, Zhuo‐Ya Mao, Ming Li, Yuying Zhang, Bang‐Guo Wei, Guoqiang Lin
Abstract
A highly regioselective approach to access amide enol carbamates and carbonates 5a–5c′, 7a–7h, and 9 was developed through Cu(OTf)2-catalyzed reactions of ynamides 4 with t-butyl carbamates 2 and 8 and t-butyl carbonates 6. Moreover, this strategy was successfully applied to generate amide enol carbamates 11a–11s and 14a–14f from imides 10 and 13 with ynamides through an N-Boc cleavage–addition ring-opening process. A range of substituents was amenable to this transformation, and the desired amide enol carbamates and carbonates were obtained in moderate to good yields.
Topics & Concepts
EnolAmideChemistryCatalysisRegioselectivityRing (chemistry)Medicinal chemistryCleavage (geology)Combinatorial chemistryOrganic chemistryMaterials scienceFracture (geology)Composite materialCatalytic Alkyne ReactionsSynthetic Organic Chemistry MethodsCatalytic C–H Functionalization Methods