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Volumn 18, Issue 52, 2012, Pages 16716-16727

Efficient synthesis of substituted 3-azabicyclo[3.1.0]hexan-2-ones from 2-iodocyclopropanecarboxamides using a copper-free Sonogashira coupling

Author keywords

acyliminium ions; cross coupling; diastereoselectivity; enamides; nitrogen heterocycles; Pictet Spengler reaction

Indexed keywords

AMIDES; AMINES; CARBON; COPPER; HYDROCARBONS; IONS; ORGANOMETALLICS; PROTONATION; STEREOSELECTIVITY;

EID: 84872895506     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203153     Document Type: Article
Times cited : (19)

References (167)
  • 37
    • 33748792796 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6029-6032
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 6029-6032
  • 51
  • 54
    • 18044386806 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2328-2334
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 2328-2334
  • 57
    • 46649098072 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4268-4315.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4268-4315
  • 75
    • 0041409651 scopus 로고    scopus 로고
    • R. Ballini, D. Fiorini, A. Palmieri, Synlett 2003, 1704-1706; for one example of cyclopropanation using a lithiated chloroallylphosphonamide, see
    • (2003) Synlett , pp. 1704-1706
    • Ballini, R.1    Fiorini, D.2    Palmieri, A.3
  • 87
    • 77949801096 scopus 로고    scopus 로고
    • For a recent approach involving the C-H bond alkenylation of a cyclopropane-carboxamide followed by ring closure through the Michael reaction, see:, M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680-3681.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3680-3681
    • Wasa, M.1    Engle, K.M.2    Yu, J.-Q.3
  • 91
    • 79957687758 scopus 로고    scopus 로고
    • For a recent approach featuring an intramolecular [4+2]-cycloaddition between a methylenecyclopropane and a β-aminoenone, see:, F. R. Petronijevic, P. Wipf, J. Am. Chem. Soc. 2011, 133, 7704-7707.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 7704-7707
    • Petronijevic, F.R.1    Wipf, P.2
  • 100
    • 84872896335 scopus 로고
    • American Cyanamid Company, Stamford (Connecticut, USA), U.S. Patent 4131611; CAN 89: 129383
    • W. J. Fanshawe, J. W. Epstein, L. S. Crawley, C. M. Hofmann, S. R. Safir, American Cyanamid Company, Stamford (Connecticut, USA), U.S. Patent 4131611; CAN 89: 129383, 1978
    • (1978)
    • Fanshawe, W.J.1    Epstein, J.W.2    Crawley, L.S.3    Hofmann, C.M.4    Safir, S.R.5
  • 101
    • 84885548397 scopus 로고    scopus 로고
    • Ranbaxy Laboratories Ltd., Gurgaon, Haryana (India), 014853; CAN 140: 199200
    • A. Mehta, A. V. Silamkoti, K. Kaur, J. B. Gupta, Ranbaxy Laboratories Ltd., Gurgaon, Haryana (India), PCT Int. Appl. 014853; CAN 140: 199200, 2004
    • (2004) PCT Int. Appl.
    • Mehta, A.1    Silamkoti, A.V.2    Kaur, K.3    Gupta, J.B.4
  • 102
    • 77949881568 scopus 로고    scopus 로고
    • Glaxo Group Ltd., Greenford Middlesex (UK), 074716; CAN 149: 104597
    • G. Bonanomi, F. Micheli, S. Terreni, Glaxo Group Ltd., Greenford Middlesex (UK), PCT Int. Appl. 074716; CAN 149: 104597, 2008,.
    • (2008) PCT Int. Appl.
    • Bonanomi, G.1    Micheli, F.2    Terreni, S.3
  • 106
    • 80052483777 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 8538-8564.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 8538-8564
  • 126
  • 154
    • 0347985383 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 5993-5996.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5993-5996
  • 166
    • 77953012537 scopus 로고    scopus 로고
    • references cited therein
    • M. L. Van Linn, J. M. Cook, J. Org. Chem. 2010, 75, 3587-3599 and references cited therein.
    • (2010) J. Org. Chem. , vol.75 , pp. 3587-3599
    • Van Linn, M.L.1    Cook, J.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.