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Diastereoselective and Stereodivergent Synthesis of 2‐Cinnamylpyrrolines Enabled by Photoredox‐Catalyzed Iminoalkenylation of Alkenes
Author(s) -
Shen Xu,
Huang Congcong,
Yuan XiangAi,
Yu Shouyun
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202016941
Subject(s) - stereocenter , diastereomer , reagent , chemistry , photoredox catalysis , dichloromethane , tetrahydrofuran , catalysis , solvent , isomerization , electron transfer , combinatorial chemistry , photocatalysis , organic chemistry , photochemistry , enantioselective synthesis
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.