Journal
ORGANIC LETTERS
Volume 24, Issue 32, Pages 6013-6017Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02288
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Funding
- NSFC [21871062, 22071035]
- Natural Science Foundation of Guangxi [2021GXNSFBA220002]
- Basic Ability Enhancement Program for Young and Middle-aged Teachers of Guangxi [2022KY0507]
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A new type of quinoxaline-derived tridentate N,N,O-ligand was synthesized and successfully applied in the synthesis of N-vinyl cinnamaldehyde nitrones with high Z-selectivity and good yields.
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.
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