Copper‐Catalyzed Enantioselective C1,N‐Dipolar (3+2) Cycloadditions of 2‐Aminoallyl Cations with Indoles
Lulu Shen, Yin Zheng, Zitong Lin, Tianzhu Qin, Zhongxing Huang, Weiwei Zi
Abstract
2-Aminoallyl cations are versatile 1,3-dipoles that could potentially be used for diverse (3+n) cycloaddition reactions. Despite some preliminary studies, the asymmetric catalytic transformation of these species is still underdeveloped. We herein report a binuclear copper-catalyzed generation of 2-aminoallyl cations from ethynyl methylene cyclic carbamates and their enantioselective (3+2) cycloaddition reaction with indoles to construct chiral pyrroloindolines. This transformation features a novel C1,N-dipolar reactivity for 2-aminoallyl cations.
Topics & Concepts
Enantioselective synthesisCycloadditionCatalysisReactivity (psychology)ChemistryCopper1,3-Dipolar cycloadditionMethyleneCombinatorial chemistryMedicinal chemistryTransformation (genetics)StereochemistryOrganic chemistryBiochemistryMedicineGenePathologyAlternative medicineSynthesis and Characterization of PyrrolesCyclopropane Reaction MechanismsAsymmetric Synthesis and Catalysis