Copper-catalyzed enantioselective intramolecular aryl C-N coupling: synthesis of enantioenriched 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxamides via an asymmetric desymmetrization strategy

Copper-catalyzed enantioselective intramolecular aryl C-N coupling: synthesis of enantioenriched 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxamides via an asymmetric desymmetrization strategy

The differentiation of two nucleophilic amide groups in malonamides through a copper-catalyzed enantioselective intramolecular aryl C-N coupling reaction is demonstrated based on an asymmetric desymmetrization strategy. Such a method afforded enantioenriched 2-oxo-1,2,3,4-tetrahydroquinoline-3-carbo...

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Veröffentlicht in:Organic letters 2015-01, Vol.17 (2), p.374-377
Hauptverfasser: He, Nian, Huo, Yanping, Liu, Jianguang, Huang, Yusha, Zhang, Shasha, Cai, Qian
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Catalysis
Copper
Molecular Structure
Quinolines - chemical synthesis
Quinolines - chemistry
Stereoisomerism
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Zusammenfassung:The differentiation of two nucleophilic amide groups in malonamides through a copper-catalyzed enantioselective intramolecular aryl C-N coupling reaction is demonstrated based on an asymmetric desymmetrization strategy. Such a method afforded enantioenriched 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxamides in high yields and moderate to good enantioselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5035386