Catalytic Asymmetric Intermolecular [3 + 2] Photocycloaddition of Cyclopropylamines with Electron-Deficient Olefins
Yating Dai, Hongchun Huang, Shuangshuang Liang, Yanli Yin, Xu Ban, Xiaowei Zhao, Zhiyong Jiang
Abstract
-arylcyclopropylamines with 2-aryl acrylates/ketones and cyclic ketone-derived terminal olefins via asymmetric photoredox catalysis is reported. A dual catalyst system involving DPZ and a chiral phosphoric acid is effective for the transformations, leading to a wide array of valuable cyclopentylamines with high yields, ee's, and drs. Among them, elaborate modulation of the ester group of 2-aryl acrylates was shown to be effective in improving reactivity, thereby enabling the success of the transformations.
Topics & Concepts
ChemistryIntermolecular forceCycloadditionCatalysisEnantioselective synthesisArylReactivity (psychology)KetonePhosphoric acidCombinatorial chemistryPhotochemistryMedicinal chemistryOrganic chemistryMoleculeAlternative medicineAlkylMedicinePathologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCO2 Reduction Techniques and Catalysts