Cation radical imino Diels-Alder reaction: A new approach for the synthesis of tetrahydroquinolines

Synlett

Volumn , Issue 11, 2003, Pages 1707-1709

  Jia, Xiaodong ^a   Lin, Hechun ^a   Huo, Congde ^a   Zhang, Wei ^a   Lü, Jianming ^a   Yang, Li ^a   Zhao, Guangyu ^a   Liu, Zhong Li ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Cation radical; Cycloaddition; Imines; Tetrahydroquinolines

Indexed keywords

AROMATIC AMINE; CATION; FURAN DERIVATIVE; IMINE; QUINOLINE DERIVATIVE; RADICAL; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLOADDITION; DIELS ALDER REACTION; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 0042912898     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40989     Document Type: Article

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29. 2), 53.9 (CH), 116.1 (C-8), 122.4 (C-6), 123.7 (C-5), 126.3 (2 C, Ph), 126.6 (2 C, Ph), 127.5 (2 C, Ph), 127.8 (2 C, Ph), 128.1 (C-7), 128.5 (2 C, Ph), 142.1 (1 C, Ph), 147.5 (1 C, Ph), 144.6 (C-10), 150.4 (C-9). The coupling constants of H-2 suggest its axial conformation in both syn- and anti-3b. The significant low-field shift of H-3e and up-field shift of H-2 of anti-3b in comparison with those of syn-3b suggests an axial 4-phenyl group in anti-3b while an equatorial 4-phenyl group in syn-3b. The stereochemistry was confirmed by their NOESY spectra which show a clear cross peak between the 4-methyl and H-2 in syn-3b, while no such correlation in anti-3b.
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32. 4