Diastereoselective and Stereodivergent Synthesis of 2‐Cinnamylpyrrolines Enabled by Photoredox‐Catalyzed Iminoalkenylation of Alkenes | Zendy

Shen Xu | Zendy; Huang Congcong | Zendy; Yuan XiangAi | Zendy; Yu Shouyun | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.202016941

Subject(s) - stereocenter , chemistry , diastereomer , reagent , photoredox catalysis , dichloromethane , isomerization , tetrahydrofuran , solvent , electron transfer , catalysis , combinatorial chemistry , photocatalysis , photochemistry , organic chemistry , 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.

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