Copper(I)-Catalyzed Ketenimine Formation/Aza-Claisen Rearrangement Cascade for Stereoselective Synthesis of α-Allylic Amidines
Chenggang Wang, Rui Wu, Ting-Peng Li, Tao Jia, Yang Li, Dongmei Fang, Xiaozhen Chen, Yuanji Gao, Hai‐Liang Ni, Ping Hu, Bi‐Qin Wang, Peng Cao
Abstract
A copper-catalyzed three-component reaction of terminal alkynes, TsN3, and tertiary allylic amines is developed toward the one-pot synthesis of α-allylic amidines. The product was synthesized on gram scale under 1 mol % of catalyst loading. Transformations of products into alkenyl amine and other nitrogen-containing compounds are demonstrated without any loss of stereochemical information.
Topics & Concepts
KetenimineChemistryAllylic rearrangementCatalysisStereoselectivityCopperClaisen rearrangementPericyclic reactionAmine gas treatingMedicinal chemistryCombinatorial chemistryOrganic chemistryChemical Synthesis and AnalysisClick Chemistry and ApplicationsSynthesis and Biological Evaluation