Diastereoselective and Stereodivergent Synthesis of 2‐Cinnamylpyrrolines Enabled by Photoredox‐Catalyzed Iminoalkenylation of Alkenes
Shen Xu, Congcong Huang, Xiang‐Ai Yuan, Shouyun Yu
Abstract
A photoredox-catalyzed iminoalkenylation of γ-alkenyl O-acyl oximes has been developed. Readily available alkenylboronic acids serve as alkenylation reagents, leading to densely functionalized pyrrolines. Both (E)- and (Z)-cinnamylpyrrolines are accessible depending on the reaction solvent. In dichloromethane, (E)-cinnamylpyrrolines are produced through a photoredox-mediated single-electron-transfer process. In tetrahydrofuran, (Z)-cinnamylpyrrolines are generated by photocatalytic contra-thermodynamic E-to-Z isomerization of (E)-cinnamylpyrrolines though an energy-transfer pathway. Two stereocenters are established with complete diastereoselectivity and only one diastereomer is isolated.
Topics & Concepts
StereocenterDiastereomerChemistryReagentPhotoredox catalysisDichloromethaneTetrahydrofuranIsomerizationCatalysisSolventCombinatorial chemistryPhotocatalysisOrganic chemistryPhotochemistryEnantioselective synthesisRadical Photochemical ReactionsFluorine in Organic ChemistrySynthesis of Indole Derivatives