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Volumn , Issue 4, 2009, Pages 371-384

Catalytic skeletal reorganization of enynes through electrophilic activation of alkynes: Double cleavage of C-C double and triple bonds

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EID: 58149458880     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b812466c     Document Type: Review
Times cited : (193)

References (113)
  • 23
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    • Fürstner et al. and Echavarren et al. independently have unearthed the diverse potential catalytic abilities of Pt catalysts. See ref. 2b and also see:
    • N. Chatani N. Furukawa H. Sakurai S. Murai Organometallics 1996 15 901
    • (1996) Organometallics , vol.15 , pp. 901
    • Chatani, N.1    Furukawa, N.2    Sakurai, H.3    Murai, S.4
  • 24
    • 7644225283 scopus 로고    scopus 로고
    • For application to the natural product synthesis using ring-expansion by the skeletal reorganization, see:
    • A. M. Echavarren C. Nevado Chem. Soc. Rev. 2004 33 431
    • (2004) Chem. Soc. Rev. , vol.33 , pp. 431
    • Echavarren, A.M.1    Nevado, C.2
  • 67
    • 0037019690 scopus 로고    scopus 로고
    • The migration of H on the substituent(s) at the olefin were often observed in the late transition metal catalyzed enyne (or enyne derivative) cycloisomerization: See ref. 11. Also other examples of enyne:
    • N. Chatani H. Inoue T. Kotsuma S. Murai J. Am. Chem. Soc. 2002 124 10294
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10294
    • Chatani, N.1    Inoue, H.2    Kotsuma, T.3    Murai, S.4
  • 74
    • 0000925182 scopus 로고
    • Chung et al. have also used this methodology to make a bicyclic eight-membered ring compound using enynes with cyclohexadienes.
    • R. Grigg P. Stevenson T. Worakun Tetrahedron 1988 44 4967
    • (1988) Tetrahedron , vol.44 , pp. 4967
    • Grigg, R.1    Stevenson, P.2    Worakun, T.3
  • 75
    • 33846013923 scopus 로고    scopus 로고
    • while Sarpong et al. have used this methodology in natural product synthesis
    • S. M. Kim S. I. Lee Y. K. Chung Org. Lett. 2006 8 5425
    • (2006) Org. Lett. , vol.8 , pp. 5425
    • Kim, S.M.1    Lee, S.I.2    Chung, Y.K.3
  • 89
    • 0037154820 scopus 로고    scopus 로고
    • Other types of alkenylations by Lewis acid through the activation of alkyne. For a recent review on metal catalyzed annulations, see:
    • H. Inoue N. Chatani S. Murai J. Org. Chem. 2002 67 1414
    • (2002) J. Org. Chem. , vol.67 , pp. 1414
    • Inoue, H.1    Chatani, N.2    Murai, S.3
  • 95
    • 0346265937 scopus 로고
    • 3 exists in the intermolecular addition of alkynes to arenes in the presence of Lewis acid catalysts. See:
    • D. A. Armitage, in Comprehensive Organometallic Chemistry, eds., S. G. Wilkinson,,, F. G. A. Stone, and, E. W. Abel,, Pergamon Press, Oxford, UK, 1982, ch. 9.1.3.5, vol. 2, pp. 47-51
    • (1982) Comprehensive Organometallic Chemistry, Eds.
    • Armitage In, D.A.1
  • 104
    • 38149016119 scopus 로고    scopus 로고
    • Mechanism for the formation of type I is shown in Scheme 21
    • H. Nakai N. Chatani Chem. Lett. 2007 36 1494
    • (2007) Chem. Lett. , vol.36 , pp. 1494
    • Nakai, H.1    Chatani, N.2


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