메뉴 건너뛰기




Volumn 132, Issue 16, 2010, Pages 5590-5591

Brønsted acid-catalyzed cascade cycloisomerization of enynes via acetylene cations and sp3-hybridized C-H bond activation

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC ENYNES; BICYCLIC COMPOUNDS; CH-BOND ACTIVATION; CYCLOISOMERIZATIONS; H-BONDS; HIGH YIELD;

EID: 77952564588     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101633x     Document Type: Article
Times cited : (61)

References (28)
  • 1
    • 77349104061 scopus 로고    scopus 로고
    • 3)-H bond activation, see
    • 3)-H bond activation, see: Bellina, F. and Rossi, R. Chem. Rev. 2010, 110, 1082
    • (2010) Chem. Rev. , vol.110 , pp. 1082
    • Bellina, F.1    Rossi, R.2
  • 6
    • 51249100498 scopus 로고    scopus 로고
    • 3)-H bond activation, see
    • 3)-H bond activation, see: Arcadi, A. Chem. Rev. 2008, 108, 3266
    • (2008) Chem. Rev. , vol.108 , pp. 3266
    • Arcadi, A.1
  • 11
    • 70450161823 scopus 로고    scopus 로고
    • 3)-H bond activation via a 1,5-hydride shift, see
    • 3)-H bond activation via a 1,5-hydride shift, see: Vadola, P. A. and Sames, D. J. Am. Chem. Soc. 2009, 131, 16525
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 16525
    • Vadola, P.A.1    Sames, D.2
  • 19
    • 4143058102 scopus 로고    scopus 로고
    • For Brønsted acid-mediated enyne cyclization, see
    • For Brønsted acid-mediated enyne cyclization, see: Zhang, L. and Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 10204
    • Zhang, L.1    Kozmin, S.A.2
  • 20
    • 77952558366 scopus 로고    scopus 로고
    • Other solvents, such as THF, toluene, and acetonitrile, were almost ineffective even under heating conditions (80 °C). Also, see ref 4
    • Other solvents, such as THF, toluene, and acetonitrile, were almost ineffective even under heating conditions (80 °C). Also, see ref 4.
  • 23
    • 77952554707 scopus 로고    scopus 로고
    • 2 = H; Table 3), the reaction reached completion in 0.5 h at room temperature, giving an inseparable mixture of the corresponding two diastereomeric bicycles 6 and its double-bond-migrated product in 85% total yield (see the Supporting Information)
    • 2 = H; Table 3), the reaction reached completion in 0.5 h at room temperature, giving an inseparable mixture of the corresponding two diastereomeric bicycles 6 and its double-bond-migrated product in 85% total yield (see the Supporting Information).
  • 28
    • 77952573929 scopus 로고    scopus 로고
    • An alternative 1,5-hydride shift mechanism is shown below
    • An alternative 1,5-hydride shift mechanism is shown below


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.