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Volumn 46, Issue 34, 2005, Pages 5629-5632

Halide trapping of the Nazarov intermediate in strained polycyclic systems: A new interrupted Nazarov reaction

Author keywords

Carbocation; Diastereoselective; Halide; Lewis acid; Nazarov cyclization

Indexed keywords

HALIDE; POLYCYCLIC HYDROCARBON;

EID: 22544443923     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.101     Document Type: Article
Times cited : (47)

References (42)
  • 9
    • 3543126652 scopus 로고    scopus 로고
    • For a related process involving asymmetric proton transfer to the Nazarov intermediate, see: G. Liang, and D. Trauner J. Am. Chem. Soc. 126 2004 9544 9545
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 9544-9545
    • Liang, G.1    Trauner, D.2
  • 23
    • 0000422935 scopus 로고
    • Denmark and Klix did observe halogen incorporation during a silyl-directed Nazarov cyclization via an apparent oxidative pathway involving the iron(III) enolate intermediate formed after elimination: S.E. Denmark, and R.C. Klix Tetrahedron 44 1988 4043 4060
    • (1988) Tetrahedron , vol.44 , pp. 4043-4060
    • Denmark, S.E.1    Klix, R.C.2
  • 25
    • 33044498913 scopus 로고    scopus 로고
    • note
    • In those cases where minor amounts of the alternative endo cyclization isomers were observed (e.g., 3b and 3c ), coupling between bridgehead protons H(3) and H(4) was clearly observed in these isomers.
  • 37
    • 33044503939 scopus 로고    scopus 로고
    • unpublished results.
    • White, T. D., unpublished results.
    • White, T.D.1
  • 39
    • 33044484097 scopus 로고    scopus 로고
    • submitted for publication.
    • We have observed that simple deprotonation of the Nazarov intermediate is slow for bridged bicyclic substrates when other termination pathways are available. For examples involving the participation of a remote alkene, see: Giese, S.; Mazzola, R. D., Jr.; Amann, C. M.; Arif, A. M.; West, F. G., submitted for publication.
    • Giese, S.1    Mazzola Jr., R.D.2    Amann, C.M.3    Arif, A.M.4    West, F.G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.