Synthesis of N‑Vinyl Cinnamaldehyde Nitrones through Atropisomeric Quinoxaline-Derived N,N,O‑Ligand-Promoted Chan-Lam Reaction

A type of quinoxaline-derived tridentate N,N,O-ligand was synthesized in good to excellent yields over three steps through iodination of 2-aryl indoles, sequential Kornblum-type oxidation with DMSO, and capture by 1,2-diaminobenzenes. The prepared atropisomeric N,N,O-ligand was successfully applied...

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Bibliographic Details
Published in:Organic letters 2022-08, Vol.24 (32), p.6013-6017
Main Authors: Chen, Hao, Wei, Cui, Pang, Guang-Li, Liang, Cui, Mo, Dong-Liang, Ma, Xiao-Pan
Format: Article
Language:English
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Summary:A type of quinoxaline-derived tridentate N,N,O-ligand was synthesized in good to excellent yields over three steps through iodination of 2-aryl indoles, sequential Kornblum-type oxidation with DMSO, and capture by 1,2-diaminobenzenes. The prepared atropisomeric N,N,O-ligand was successfully applied in the synthesis of N-vinyl cinnamaldehyde nitrones as only Z-isomers in good yields through the Chan-Lam reaction. The method features an easily accessed tunable tridentate N,N,O-ligand, broad substrate scope, good functional group tolerance, and high Z-isomer for N-vinyl nitrones.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02288