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Volumn 12, Issue 8, 2010, Pages 1696-1699

Highly stereoselective 7-endo-trig /ring contraction cascade to construct pyrrolo[1,2- a ]quinoline derivatives

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE; QUINOLINE DERIVATIVE;

EID: 77951196624     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100220c     Document Type: Article
Times cited : (45)

References (41)
  • 1
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    • For a recent review on the synthesis of hydroquinolines, see:, and references therein
    • For a recent review on the synthesis of hydroquinolines, see: Kouznetsov, V. V. Tetrahedron 2009, 65, 2721-2750 and references therein
    • (2009) Tetrahedron , vol.65 , pp. 2721-2750
    • Kouznetsov, V.V.1
  • 9
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    • Several approaches to synthesize lactones via the phenonium ion intermediate were reported, however, application of phenonium ion in synthetic chemistry is rather unexplored. See
    • Several approaches to synthesize lactones via the phenonium ion intermediate were reported, however, application of phenonium ion in synthetic chemistry is rather unexplored. See
  • 16
    • 77951190706 scopus 로고    scopus 로고
    • For methods to construct 4-substituted pyrrolo[1,2- a ]quinolines, see
    • For methods to construct 4-substituted pyrrolo[1,2- a ]quinolines, see
  • 20
    • 77951201136 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 21
    • 77951169569 scopus 로고    scopus 로고
    • For a comprehensive review dedicated to the N -acyliminium ion cyclization, see
    • For a comprehensive review dedicated to the N -acyliminium ion cyclization, see
  • 23
    • 77951171179 scopus 로고    scopus 로고
    • 19F NMR spectrum of the unpurified mixtures, 3aa (X = OTFA) was observed as the major product. The relative configuration was deduced from the hydrolyzed product (X = OH).
    • 19F NMR spectrum of the unpurified mixtures, 3aa (X = OTFA) was observed as the major product. The relative configuration was deduced from the hydrolyzed product (X = OH).
  • 24
    • 77951167634 scopus 로고    scopus 로고
    • For the convenience of discussion, the nomenclature of cyclized products 3 and 4 is based on the core structures such as the quinoline ring and 1-benzazepine ring, respectively
    • For the convenience of discussion, the nomenclature of cyclized products 3 and 4 is based on the core structures such as the quinoline ring and 1-benzazepine ring, respectively.
  • 25
    • 77951159555 scopus 로고    scopus 로고
    • A free N -acyliminium ion intermediate should result in identical rate and product distribution; however, experimental results in Table 1 may imply a tight ion pair with the counterion or a complex with the Lewis acid used. This scenario was widely recognized in the Friedel-Crafts reaction
    • A free N -acyliminium ion intermediate should result in identical rate and product distribution; however, experimental results in Table 1 may imply a tight ion pair with the counterion or a complex with the Lewis acid used. This scenario was widely recognized in the Friedel-Crafts reaction; see
  • 28
    • 38149016915 scopus 로고    scopus 로고
    • For a recent review on fluorine compounds, see
    • For a recent review on fluorine compounds, see: O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 308-319
    • O'hagan, D.1
  • 30
    • 77951152315 scopus 로고    scopus 로고
    • note
    • The neighboring effect of the methyl group is not clear. One proposed explanation is that the o -methyl group may participate in the stabilization of phenonium ion through a C-H hyperconjugation.
  • 31
    • 77951159738 scopus 로고    scopus 로고
    • note
    • However, the origin of exceedingly high stereoselectivity needs to be further investigated with the assistance of computational calculation.
  • 32
    • 77951179078 scopus 로고    scopus 로고
    • note
    • 4.
  • 34
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    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, pp 563 - 593.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 563-593
    • Fleming, I.1
  • 35
    • 77951195348 scopus 로고    scopus 로고
    • note
    • 3 in 1,4-dioxane, however, this protocol resulted in inseparable alkene isomers; see
  • 37
    • 77951153435 scopus 로고    scopus 로고
    • For selected complex natural products bearing pyrroloquinoline, see
    • For selected complex natural products bearing pyrroloquinoline, see
  • 41
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    • For an advance intermediate in the total synthesis of gephyrotoxin
    • For an advance intermediate in the total synthesis of gephyrotoxin: Ito, Y.; Nakajo, E.; Nakatsuka, M.; Saegusa, T. Tetrahedron Lett. 1983, 24, 2881-2884
    • (1983) Tetrahedron Lett. , vol.24 , pp. 2881-2884
    • Ito, Y.1    Nakajo, E.2    Nakatsuka, M.3    Saegusa, T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.