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Volumn 128, Issue 51, 2006, Pages 16500-16501

W(CO)5(L)-catalyzed tandem intramolecular cyclopropanation/cope rearrangement for the stereoselective construction of bicyclo[5.3.0]decane framework

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CYCLOALKANE DERIVATIVE;

EID: 33845949244     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0671924     Document Type: Article
Times cited : (39)

References (24)
  • 5
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    • Unpublished result.
    • Unpublished result.
  • 6
    • 33747175365 scopus 로고    scopus 로고
    • For recent reviews of the reactions through cyclopropyl carbene complex intermediates generated from enynes, see: (a) Nieto-Oberhuber, C, López, S, Jiménez-Núñez, E, Echavarren, A. M. Chem.-Eur. J. 2006, 12, 5916
    • For recent reviews of the reactions through cyclopropyl carbene complex intermediates generated from enynes, see: (a) Nieto-Oberhuber, C.; López, S.; Jiménez-Núñez, E.; Echavarren, A. M. Chem.-Eur. J. 2006, 12, 5916.
  • 9
    • 15644378136 scopus 로고
    • For reviews on the Cope rearrangement of divinylcyclopropanes to form a seven-membered ring system, see: a
    • For reviews on the Cope rearrangement of divinylcyclopropanes to form a seven-membered ring system, see: (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y. C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
    • (1989) Chem. Rev , vol.89 , pp. 165
    • Wong, H.N.C.1    Hon, M.-Y.2    Tse, C.-W.3    Yip, Y.C.4    Tanko, J.5    Hudlicky, T.6
  • 12
    • 0000065841 scopus 로고
    • Trost, B. M, Ed, Pergamon Press: Oxford
    • (d) Piers, E. In Comprehensive Organic Synthesis: Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5. pp 971-998.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 971-998
    • Piers, E.1
  • 13
    • 33845932082 scopus 로고    scopus 로고
    • A small amount of bicyclo[3.3.0]octane derivative was obtained in 3% yield (entry 2) and 4% yield entry 3
    • A small amount of bicyclo[3.3.0]octane derivative was obtained in 3% yield (entry 2) and 4% yield (entry 3).
  • 14
    • 33845931839 scopus 로고    scopus 로고
    • In the case of cationic gold complex entry 7, protonated product of the first cyclization intermediate C was obtained in 75% yield
    • In the case of cationic gold complex (entry 7), protonated product of the first cyclization intermediate C was obtained in 75% yield.
  • 16
    • 33845940660 scopus 로고    scopus 로고
    • In the presence of 10 mol, of NEt3 the conditions of Table 1, entry 3, the reaction of alkyne 7 was not completed in 30 h
    • 3 (the conditions of Table 1, entry 3), the reaction of alkyne 7 was not completed in 30 h.
  • 21
    • 33644662974 scopus 로고    scopus 로고
    • For other examples of the synthesis of bicyclo[5.3.0]decane derivatives through the Cope rearrangement of divinylcyclopropane using diazo compounds, see: (a) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 2609.
    • For other examples of the synthesis of bicyclo[5.3.0]decane derivatives through the Cope rearrangement of divinylcyclopropane using diazo compounds, see: (a) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 2609.
  • 23
    • 0000761476 scopus 로고    scopus 로고
    • Using carbene complexes, see: Harvey, D. F, Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066
    • (c) Using carbene complexes, see: Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066.
  • 24
    • 0142165973 scopus 로고    scopus 로고
    • For generation of divinylcyclopropane by cyclopropanation of dienes using propargylic carboxylates and ruthenium catalyst, see: Miki, K, Ohe, K, Uemura, S. J. Org. Chem. 2003, 68, 8505
    • For generation of divinylcyclopropane by cyclopropanation of dienes using propargylic carboxylates and ruthenium catalyst, see: Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.