메뉴 건너뛰기




Volumn 129, Issue 44, 2007, Pages 13455-13463

Oxygen donor-mediated equilibration of diastereomeric alkene-palladium(II) intermediates in enantioselective desymmetrizing heck cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; LIGANDS; OLEFINS; PALLADIUM; STEREOCHEMISTRY;

EID: 35948942033     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072571y     Document Type: Article
Times cited : (38)

References (74)
  • 9
    • 0012857368 scopus 로고    scopus 로고
    • Overman, L. E, Ed, Wiley: New York
    • Link, J. T. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York 2002; Vol. 60, pp 157-534.
    • (2002) Organic Reactions , vol.60 , pp. 157-534
    • Link, J.T.1
  • 22
    • 33751275280 scopus 로고    scopus 로고
    • A 3,6-dimethoxy-functionalized substrate 5 (n = 1) was of particular interest to us as its cyclization would provide a catalytic asymmetric access to the AB-ring synthon of anthracycline antibiotics: Oestreich, M.; Sempere-Culler, F.; Machotta, A. B. Synlett 2006, 2965-2968.
    • A 3,6-dimethoxy-functionalized substrate 5 (n = 1) was of particular interest to us as its cyclization would provide a catalytic asymmetric access to the AB-ring synthon of anthracycline antibiotics: Oestreich, M.; Sempere-Culler, F.; Machotta, A. B. Synlett 2006, 2965-2968.
  • 26
    • 35248881019 scopus 로고    scopus 로고
    • Oestreich, M. Directed Mizoroki-Heck Reactions; Chatani, N., Ed.; Topics in Organometallic Chemistry; Springer: Heidelberg, 2007; http://dx.doi.org/10.1007/3418_2007_063.
    • (b) Oestreich, M. Directed Mizoroki-Heck Reactions; Chatani, N., Ed.; Topics in Organometallic Chemistry; Springer: Heidelberg, 2007; http://dx.doi.org/10.1007/3418_2007_063.
  • 41
    • 35948987524 scopus 로고    scopus 로고
    • Jaguar 6.5; Schrödinger, Inc.: Portland, OR, U.S.A., 2006.
    • (d) Jaguar 6.5; Schrödinger, Inc.: Portland, OR, U.S.A., 2006.
  • 46
    • 84986468715 scopus 로고    scopus 로고
    • Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; v. R. Schleyer, P. J. Comput. Chem. 1983, 4, 294-301.
    • (i) Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; v. R. Schleyer, P. J. Comput. Chem. 1983, 4, 294-301.
  • 57
  • 59
    • 35948995686 scopus 로고    scopus 로고
    • (d) http://www.iupac.org/goldbook/C01480.pdf.
  • 60
    • 35948954692 scopus 로고    scopus 로고
    • We also wondered whether hydrogen bonding of the hydroxy group to the triflate might facilitate the activation of the substrate's Ar-OTf bond by enhancing the triflate's leaving group capability. However, the reactions of the methoxy derivative and the deoxygenized substrate operate at comparable rates
    • We also wondered whether hydrogen bonding of the hydroxy group to the triflate might facilitate the activation of the substrate's Ar-OTf bond by enhancing the triflate's leaving group capability. However, the reactions of the methoxy derivative and the deoxygenized substrate operate at comparable rates.
  • 71
    • 0023732619 scopus 로고    scopus 로고
    • Overman presented evidence for a unique directing effect of an alkene unit in a diastereoselective Heck cyclization. We had also considered such an interaction in our system (E,E)-9, but unselective ring closure of (E,E)-12 dispelled this idea (Table 1, a) Earley, W. G, Oh, T, Overman, L. E. Tetrahedron Lett. 1988, 29, 3785-3788
    • Overman presented evidence for a unique directing effect of an alkene unit in a diastereoselective Heck cyclization. We had also considered such an interaction in our system (E,E)-9, but unselective ring closure of (E,E)-12 dispelled this idea (Table 1): (a) Earley, W. G.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3785-3788.
  • 74
    • 35948938904 scopus 로고    scopus 로고
    • Diploma Thesis, Albert-Ludwigs-Universität, Freiburg, Germany
    • Sempere-Culler, F. Diploma Thesis, Albert-Ludwigs-Universität, Freiburg, Germany, 2004.
    • (2004)
    • Sempere-Culler, F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.