Catalytic Asymmetric Intermolecular [3+2] Photocycloaddition of Cyclopropylamines with Electron-Deficient Olefins

An enantioselective intermolecular [3 + 2] cycloadditionof N-arylcyclopropylamines with 2-aryl acrylates/ketonesandcyclic ketone-derived terminal olefins via asymmetric photoredox catalysisis reported. A dual catalyst system involving DPZ and a chiral phosphoricacid is effective for the transformations, leading to a wide arrayof valuable cyclopentylamines with high yields, ee's, and drs.Among them, elaborate modulation of the ester group of 2-aryl acrylateswas shown to be effective in improving reactivity, thereby enablingthe success of the transformations.

Automated summary

In this study, an enantioselective intermolecular [3 + 2] cycloaddition of N-arylcyclopropylamines with 2-aryl acrylates/ketones and cyclic ketone-derived terminal olefins via asymmetric photoredox catalysis was reported. A dual catalyst system involving DPZ and a chiral phosphoric acid was effective for the transformations, leading to a wide array of valuable cyclopentylamines with high yields, ee's, and drs. 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.