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Volumn 38, Issue 10, 1999, Pages 1452-1454

Two new modes of Pd-catalyzed domino-tetracyclization of bromodienynes - 5-exo-trig cyclization wins over β-hydride elimination

Author keywords

Cross coupling; Cyclizations; Domino reactions; Heck reactions; Palladium

Indexed keywords

2 BROMODODECA 1,11 DIENE 6 YNE; 2 BROMOTRIDECA 1,12 DIENE 7 YNE; PALLADIUM; UNCLASSIFIED DRUG;

EID: 0033577877     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990517)38:10<1452::AID-ANIE1452>3.0.CO;2-P     Document Type: Article
Times cited : (72)

References (27)
  • 1
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    • For recent reviews on domino and other sequential reactions see: a) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
    • (1996) Chem. Rev. , vol.96 , pp. 115-136
    • Tietze, L.F.1
  • 13
    • 0001603937 scopus 로고
    • (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford
    • R. Grigg, V. Sridharan in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, p. 299-322.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 299-322
    • Grigg, R.1    Sridharan, V.2
  • 17
    • 0007839757 scopus 로고    scopus 로고
    • For a related all-intramolecular domino reaction of 2-substituted 1-ene-6,11-diynes and homologues to yield tricyclic skeletons with three-membered rings see: C. H. Oh, J. H. Kang, C. Y. Rhim, J. H. Kim, Chem. Lett. 1998, 375-376.
    • (1998) Chem. Lett. , pp. 375-376
    • Oh, C.H.1    Kang, J.H.2    Rhim, C.Y.3    Kim, J.H.4
  • 18
    • 33747578019 scopus 로고    scopus 로고
    • note
    • Compounds 6, 9, 12a, 16 were easily assembled in five to eight steps according to routine procedures using malonate alkylations and alkynyl-Grignard additions to aldehydes as C-C bond forming steps with appropriate building blocks.
  • 19
    • 33747565349 scopus 로고    scopus 로고
    • note
    • All new compounds were fully characterized by NMR, IR, and mass spectral data as well as by elemental analyses or high-resolution mass spectra.
  • 22
    • 33847305280 scopus 로고
    • Palladium-catalyzed eight-membered ring closures are quite rare: S. E. Gibson (née Thomas), R. J. Middleton, J. Chem. Soc. Chem. Commun. 1995, 1743-1744;
    • (1995) J. Chem. Soc. Chem. Commun. , pp. 1743-1744
    • Middleton, R.J.1
  • 24
    • 33747554105 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-103255 (cis-17), CCDC-103256 (14a), and CCDC-103257 (epoxide from 11a). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
  • 25
    • 0001056659 scopus 로고
    • Such a γ-hydride elimination is equivalent to a γ-C-H activation. δ-C-H activation on a tert-butyl group has been reported: G. Dyker, Angew. Chem. 1994, 106, 117-119;
    • (1994) Angew. Chem. , vol.106 , pp. 117-119
    • Dyker, G.1
  • 27
    • 0032500353 scopus 로고    scopus 로고
    • Metal carbene (including platinum carbene) complexes have been invoked in cascade cyclizations of 1,6-diene-11-ynes to yield cyclopropane-linked tetracyclic systems, yet in the reported cases they were not formed by α-dehydrobromination: N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 9104-9105
    • Chatani, N.1    Kataoka, K.2    Murai, S.3    Furukawa, N.4    Seki, Y.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.