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Volumn 126, Issue 49, 2004, Pages 15978-15979

Gold(I)-catalyzed propargyl claisen rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ESTER DERIVATIVE; GOLD DERIVATIVE; OXYGEN; SILANE DERIVATIVE;

EID: 10344253858     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044602k     Document Type: Article
Times cited : (326)

References (46)
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    • (e) Frauenrath, H. In Houben-Weyl; Helmchen, G., Hoffman, R. W., Mulzer, J., Schaumann, E., Eds.: Thieme Stuttgart: New York, 1995; Vol. E 21d. p 3301.
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    • For reviews on catalysis of the Claisen rearrangement, see: (a) Lutz, R. P. Chem. Rev. 1984, 84, 205. (b) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (c) Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 1461.
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    • Lutz, R.P.1
  • 7
    • 0002967769 scopus 로고    scopus 로고
    • For reviews on catalysis of the Claisen rearrangement, see: (a) Lutz, R. P. Chem. Rev. 1984, 84, 205. (b) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (c) Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 1461.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 43
    • Ito, H.1    Taguchi, T.2
  • 8
    • 0036090871 scopus 로고    scopus 로고
    • For reviews on catalysis of the Claisen rearrangement, see: (a) Lutz, R. P. Chem. Rev. 1984, 84, 205. (b) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43. (c) Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 1461.
    • (2002) Eur. J. Org. Chem. , pp. 1461
    • Hiersemann, M.1    Abraham, L.2
  • 22
    • 8744259772 scopus 로고    scopus 로고
    • (g) For an excellent review of homogeneous gold-catalyzed reactions, see: Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
    • (2004) Gold Bull. , vol.37 , pp. 51
    • Hashmi, A.S.K.1
  • 27
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    • (e) For a review of pericyclic reactions of acetylenic compounds, see: Viola, A.; Collins, J. J.; Filipp, N. Tetrahedron 1981, 37, 3765.
    • (1981) Tetrahedron , vol.37 , pp. 3765
    • Viola, A.1    Collins, J.J.2    Filipp, N.3
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    • note
    • Attempts to isolate the aldehyde met with substantial decomposition; therefore, intermediate aldehydes were reduced in situ to allow for product purification.
  • 30
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    • note
    • 4.
  • 38
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    • note
    • 4, and the latter is not a competent catalyst.
  • 39
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    • The allene absolute stereochemistry was assigned by comparison of the optical rotation of 15: Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 10470
    • Wan, Z.1    Nelson, S.G.2
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    • For a review on the reactions of allenylsilanes, see: Masse. C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
    • (1995) Chem. Rev. , vol.95 , pp. 1293
    • Masse, C.E.1    Panek, J.S.2
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    • note
    • 13 cyclization of 7.
  • 44
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    • For a discussion on the transition state of the thermal propargyl Cope rearrangement, see: (a) Owens, K. A.; Berson, J. A. J. Am. Chem. Soc. 1990, 112, 5973. (b) Black, K. A.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1998, 120, 5622.
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    • For a discussion on the transition state of the thermal propargyl Cope rearrangement, see: (a) Owens, K. A.; Berson, J. A. J. Am. Chem. Soc. 1990, 112, 5973. (b) Black, K. A.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1998, 120, 5622.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5622
    • Black, K.A.1    Wilsey, S.2    Houk, K.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.