Electrochemically‐Driven Organocatalytic Enantioselective Oxidative Coupling of Tetrahydroisoquinolines and Acrylaldehyde

Abstract An electrochemically‐driven organocatalytic enantioselective oxidative coupling of tetrahydroisoquinolines and acrylaldehyde was developed. Various chiral C1‐alkenyl tetrahydroisoquinolines derivatives were obtained with 69–86% yields and 93:7–96:4 er. Notable features of this reaction incl...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-10, Vol.365 (20), p.3455-3460
Main Authors: Zhang, Qi‐Ying, Li, Lu‐Xin, Wang, Song‐Lin, Ma, Jing, Guo, Hai‐Ming
Format: Article
Language:English
Subjects:
Coupling
Enantiomers
Optical activity
Oxidizing agents
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Summary:Abstract An electrochemically‐driven organocatalytic enantioselective oxidative coupling of tetrahydroisoquinolines and acrylaldehyde was developed. Various chiral C1‐alkenyl tetrahydroisoquinolines derivatives were obtained with 69–86% yields and 93:7–96:4 er. Notable features of this reaction include asymmetric organocatalysis (5.0 mol% β‐ICD as catalyst), electricity as the oxidant, air atmosphere, and undivided cell. This synthetic route offers access to various optically active C1‐substituted tetrahydroisoquinolines derivatives.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300766