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Volumn 47, Issue 39, 2008, Pages 7534-7538

The role of bent acyclic allene gold complexes in axis-to-center chirality transfers

Author keywords

Allenes; Cycloisomerization; Density functional calculations; Gold; Homogeneous catalysis

Indexed keywords


EID: 54749142736     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802332     Document Type: Article
Times cited : (118)

References (68)
  • 1
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    • For recent reviews on stereoselective gold catalysis involving allenes, see: a
    • For recent reviews on stereoselective gold catalysis involving allenes, see: a) N. Bongers, N. Krause, Angew. Chem. 2008, 120, 2208;
    • (2008) Angew. Chem , vol.120 , pp. 2208
    • Bongers, N.1    Krause, N.2
  • 4
    • 54849171900 scopus 로고
    • For reviews on transition metal-allene complexes, see: a, Ed, S. R. Landor, Academic Press, London
    • For reviews on transition metal-allene complexes, see: a) T. L. Jacobs in The Chemistry of the Allenes, Vol. 2 (Ed.: S. R. Landor), Academic Press, London, 1982, pp. 277;
    • (1982) The Chemistry of the Allenes , vol.2 , pp. 277
    • Jacobs, T.L.1
  • 8
    • 0012206131 scopus 로고
    • For experimental evidence of the coordination of copper, silver, and gold to the allene central carbon, see
    • For experimental evidence of the coordination of copper, silver, and gold to the allene central carbon, see: J. H. B. Chenier, J. A. Howard, B. Mile, J. Am. Chem. Soc. 1985, 107, 4190.
    • (1985) J. Am. Chem. Soc , vol.107 , pp. 4190
    • Chenier, J.H.B.1    Howard, J.A.2    Mile, B.3
  • 15
    • 54749120983 scopus 로고    scopus 로고
    • Bent allenes can also exist as such: see Ref. [5] and references therein. For theoretical evidence, see: R. Tonner, G. Frenking, Angew. Chem. 2007, 119, 8850;
    • Bent allenes can also exist as such: see Ref. [5] and references therein. For theoretical evidence, see: R. Tonner, G. Frenking, Angew. Chem. 2007, 119, 8850;
  • 18
    • 54849171800 scopus 로고    scopus 로고
    • For recent reviews on gold-mediated homogeneous catalysis, see: a
    • For recent reviews on gold-mediated homogeneous catalysis, see: a) V. Michelet, P. Y. Toullec, J.-P. Genêt, Angew. Chem. 2008, 120, 4338;
    • (2008) Angew. Chem , vol.120 , pp. 4338
    • Michelet, V.1    Toullec, P.Y.2    Genêt, J.-P.3
  • 31
    • 0000177104 scopus 로고    scopus 로고
    • For selected examples, see: a
    • For selected examples, see: a) A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537;
    • (2001) Org. Lett , vol.3 , pp. 2537
    • Hoffmann-Röder, A.1    Krause, N.2
  • 46
    • 54749130822 scopus 로고    scopus 로고
    • M. J. Frisch et al., Gaussian 03, Gaussian, Inc., Pittsburgh, PA, 2003. DFT/B3LYP/LACVP(d,p) calculations. This methodology gave a very good agreement between computed and X-ray structures of the bent allene complexes reported in Refs. [5] and [6] (see Supporting Information).
    • M. J. Frisch et al., Gaussian 03, Gaussian, Inc., Pittsburgh, PA, 2003. DFT/B3LYP/LACVP(d,p) calculations. This methodology gave a very good agreement between computed and X-ray structures of the bent allene complexes reported in Refs. [5] and [6] (see Supporting Information).
  • 52
    • 54749148805 scopus 로고    scopus 로고
    • 3 has been used as catalyst for intermolecular hydroamination of allenes resulting in chirality transfer: see Ref. [11a].
    • 3 has been used as catalyst for intermolecular hydroamination of allenes resulting in chirality transfer: see Ref. [11a].
  • 53
    • 54749151489 scopus 로고    scopus 로고
    • Failed attempts led to allene complexes of type I, and no complex of type II′ could be found.
    • Failed attempts led to allene complexes of type I, and no complex of type II′ could be found.
  • 54
    • 32244445098 scopus 로고    scopus 로고
    • see Ref. [13b], and: a L. Zhang, S. Wang, J. Am. Chem. Soc. 2006, 128, 1442;
    • see Ref. [13b], and: a) L. Zhang, S. Wang, J. Am. Chem. Soc. 2006, 128, 1442;
  • 59
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    • -1, respectively.
    • -1, respectively.
  • 62
    • 33750497627 scopus 로고    scopus 로고
    • For recent examples, see Ref. [13b] and: a C. H. Oh, A. Kim, W. Park, D. I. Park, N. Kim, Synlett 2006, 2781;
    • For recent examples, see Ref. [13b] and: a) C. H. Oh, A. Kim, W. Park, D. I. Park, N. Kim, Synlett 2006, 2781;
  • 66
    • 54749149877 scopus 로고    scopus 로고
    • [13b] and on the basis of an X-ray analysis (see Supporting information). The absolute configuration of 35 was confirmed by circular dichroism after hydrolysis into the corresponding ketone (see Supporting information).
    • [13b] and on the basis of an X-ray analysis (see Supporting information). The absolute configuration of 35 was confirmed by circular dichroism after hydrolysis into the corresponding ketone (see Supporting information).


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