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Volumn , Issue 3, 1997, Pages 533-540

Diastereoselective synthesis of 1-hydroxy-substituted benzo[b]quinolidines and 11-hydroxy-substituted azepino[1,2-b]isoquinolines via hetero-ene cyclization

Author keywords

Azepino 1,2 b isoquinolines; Benzo b quinolidines; Cyclizations; Ene reaction; Lewis acid catalysis; Nitrogen heterocycles

Indexed keywords


EID: 0006715443     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970314     Document Type: Article
Times cited : (19)

References (54)
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  • 17
    • 0000657627 scopus 로고
    • For a tin-mediated diastereoselective radical cyclization leading to 4-oxo-benzo[3,4-b]quinolidine see: A. L. J. Beckwith, S. P. Joseph, T. A. Roshan, J. Org. Chem. 1993, 53, 4198-4199.
    • (1993) J. Org. Chem. , vol.53 , pp. 4198-4199
    • Beckwith, A.L.J.1    Joseph, S.P.2    Roshan, T.A.3
  • 29
    • 33748844552 scopus 로고    scopus 로고
    • A completely different coupling pattern for 11a-H (and 1-H as well) would be expected if the configuration of 1-H and/or 2-H was inverted
    • A completely different coupling pattern for 11a-H (and 1-H as well) would be expected if the configuration of 1-H and/or 2-H was inverted.
  • 30
    • 33748827624 scopus 로고    scopus 로고
    • note
    • Further details of the crystal structure investigations are available on request from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftliche Information mbH, D-76344 Eggenstein-Leopoldshafen, on quoting the depository number CSD-405683.
  • 31
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    • Reviews on ene reactions: [28a] H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597-617;
    • (1969) Angew. Chem. , vol.81 , pp. 597-617
    • Hoffmann, H.M.R.1
  • 35
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    • (Ed.: B. M. Trost), Pergamon Press, Oxford
    • [28c] B. B. Snider, in Comprehensive Organic Synthesis, vol. 5 (Ed.: B. M. Trost), Pergamon Press, Oxford, 1991, 1-27.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1-27
    • Snider, B.B.1
  • 39
    • 0001290261 scopus 로고
    • (Ed.: B. M. Trost), Pergamon Press, Oxford
    • [29c] B. B. Snider, in Comprehensive Organic Synthesis, vol. 2 (Ed.: B. M. Trost), Pergamon Press, Oxford, 1991, 527-561.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 527-561
    • Snider, B.B.1
  • 54
    • 33748844122 scopus 로고    scopus 로고
    • note
    • The aldehydes 10 and 19 were immediately cyclized because attempts to purify them by flash chromatography or Kugelrohr distillation resulted in complete racemization. The same result was also observed, when they were stored for 12 h at +4°C under argon.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.