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Volumn 50, Issue 39, 2011, Pages 9062-9065

Ruthenium-catalyzed coupling of oxabenzonorbornadienes with alkynes bearing a propargylic oxygen atom: Access to stereodefined benzonorcaradienes

Author keywords

alkynes; benzonorcaradienes; coupling reactions; homogeneous catalysis; ruthenium

Indexed keywords

ALKYNES; BENZONORCARADIENES; COUPLING REACTIONS; DIASTEREO-SELECTIVITY; HOMOGENEOUS CATALYSIS; OXYGEN ATOM;

EID: 80052857426     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201104589     Document Type: Article
Times cited : (36)

References (42)
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    • For inter- and intramolecular ruthenium-catalyzed couplings of alkynes with alkenes occurring with structural reorganization, see: B. M. Trost, G. Dyker, R. J. Kulawiec, J. Am. Chem. Soc. 1990, 112, 7809-7811
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  • 17
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    • For a divergent pathway in the coupling of oxabenzonorbornadiene with propargyl alcohols, thus leading to isochromenes, see: K. Villeneuve, W. Tam, Eur. J. Org. Chem. 2006, 5449-5453
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    • Villeneuve, K.1    Tam, W.2
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    • The formation of dihydronaphthofurans through rhodium-catalyzed cross-coupling of oxabenzonorbornadienes with an electron-poor alkyne (DMAD) was recently reported, see.
    • The formation of dihydronaphthofurans through rhodium-catalyzed cross-coupling of oxabenzonorbornadienes with an electron-poor alkyne (DMAD) was recently reported, see:, T. Nishimura, T. Kawamoto, K. Sasaki, E. Tsurumaki, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 1492-1493.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 1492-1493
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    • The propensity of endo-benzonorcaradienes bearing an electron-withdrawing group to undergo thermal isomerization to the more stable exo- benzonorcaradienes is well established, see for instance: W. Adam, M. Ahrweiler, M. Balci, O. Çakmak, C. R. Saha-Möller, Tetrahedron Lett. 1995, 36, 1429-1430
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1429-1430
    • Adam, W.1    Ahrweiler, M.2    Balci, M.3    Çakmak, O.4    Saha-Möller, C.R.5
  • 23
    • 0342647446 scopus 로고    scopus 로고
    • The thermal stability of endo-benzonorcaradienes 13 - 15 could be attributed to the presence of a methyl substituent on the cyclopropane.
    • P. Müller, J.-L. Toujas, G. Bernardinelli, Helv. Chim. Acta 2000, 83, 1525-1534. The thermal stability of endo-benzonorcaradienes 13-15 could be attributed to the presence of a methyl substituent on the cyclopropane.
    • (2000) Helv. Chim. Acta , vol.83 , pp. 1525-1534
    • Müller, P.1    Toujas, J.-L.2    Bernardinelli, G.3
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    • Angew. Chem. Int. Ed. 2005, 44, 6630-6666
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 6630-6666
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    • For the term "alicyclic Claisen rearrangement", see:, for examples of these rearrangements forming cyclopropyl-substituted carbonyl compounds, see
    • For the term "alicyclic Claisen rearrangement", see:, M. M. Abelman, R. L. Funk, J. D. Munger, Jr., J. Am. Chem. Soc. 1982, 104, 4030-4032, for examples of these rearrangements forming cyclopropyl-substituted carbonyl compounds, see
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    • Abelman, M.M.1    Funk, R.L.2    Munger Jr., J.D.3
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    • For a synthesis of benzonorcaradienes through gold(I)-catalyzed [4+3] annulation of styrenes with 1,3-diynes, see.
    • For a synthesis of benzonorcaradienes through gold(I)-catalyzed [4+3] annulation of styrenes with 1,3-diynes, see:, D. J. Gorin, P. Dubé, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 14480-14481.
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    • Gorin, D.J.1    Dubé, P.2    Toste, F.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.