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Volumn 16, Issue 32, 2010, Pages 9818-9828

Erratum: Synthesis of diverse indole-containing scaffolds by gold(I)-catalyzed tandem reactions of 3-propargylindoles initiated by 1,2-indole migrations: Scope and computational studies (Chemistry - A European Journal (2010) 16 DOI: 10.1002/chem.201001162);Synthesis of diverse indole-containing scaffolds by gold(I)-catalyzed tandem reactions of 3-propargylindoles initiated by 1,2-indole migrations: Scope and computational studies

Author keywords

Gold; Homogeneous catalysis; Indoles; Reaction mechanisms; gold; homogeneous catalysis; indoles; reaction mechanisms

Indexed keywords

ALCOHOLS; CARBOXYLATION; CATALYSIS; CYCLIZATION; GOLD; REACTION INTERMEDIATES; SCAFFOLDS; SULFUR COMPOUNDS;

EID: 77955905571     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103118     Document Type: Erratum
Times cited : (58)

References (106)
  • 2
    • 34250824768 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 3410 -3449;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3410-3449
  • 5
    • 46649098072 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4268 -4315;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4268-4315
  • 9
    • 34249006882 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 2750-2752;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 2750-2752
  • 21
    • 53249094195 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7354-7357.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7354-7357
  • 23
    • 28844458694 scopus 로고    scopus 로고
    • See, for instance: a) L. Zhang, J. Am. Chem. Soc. 2005, 127, 16804-16805;
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 16804-16805
    • Zhang, L.1
  • 25
    • 33746081826 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1105-1109;
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1105-1109
  • 41
    • 77955895325 scopus 로고    scopus 로고
    • 6, resulted to be useful catalysts for this transformation (see the Supporting Information)
    • 6, resulted to be useful catalysts for this transformation (see the Supporting Information).
  • 42
    • 25444522675 scopus 로고    scopus 로고
    • For bis(trifluoromethanesulfonyl)imidate-based gold catalysts, see: N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133-4136.
    • (2005) Org. Lett. , vol.7 , pp. 4133-4136
    • Mézailles, N.1    Ricard, L.2    Gagosz, F.3
  • 43
    • 77955894995 scopus 로고    scopus 로고
    • CCDC-689754 (3c), 689755 (3e), 689757 (4a), 689756 (4b), and 772902 (13b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC-689754 (3c), 689755 (3e), 689757 (4a), 689756 (4b), and 772902 (13b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 51
    • 70349934598 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 6152-6155;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6152-6155
  • 53
    • 70350590888 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 8757-8760.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 8757-8760
  • 72
    • 77955913039 scopus 로고    scopus 로고
    • The syn/anti conformations about the C3-C1′ bond were also considered (see the Supporting Information), but their effect on activation energies and product outcome was negligible. See Supporting Information for a complete stereochemical depiction of the reaction course and the computational analysis of the alternative pathways
    • The syn/anti conformations about the C3-C1′ bond were also considered (see the Supporting Information), but their effect on activation energies and product outcome was negligible. See Supporting Information for a complete stereochemical depiction of the reaction course and the computational analysis of the alternative pathways.
  • 73
    • 77955901938 scopus 로고    scopus 로고
    • Strikingly, this bond reaches 1.79 Å in the stereoisomer that originates from the syn coordination of gold (see Supporting Information) in an almost barrierless process
    • Strikingly, this bond reaches 1.79 Å in the stereoisomer that originates from the syn coordination of gold (see Supporting Information) in an almost barrierless process.
  • 74
    • 68349132826 scopus 로고    scopus 로고
    • There are authoritative reports in the literature that advocate for a careful use of the term carbene in gold-catalyzed mechanisms and describe these structures as resulting from a p Lewis activation by gold that makes the adjacent carbon more electrophilic, or even a carbocation: a) G. Seidel, R. Mynott, A. Fürstner, Angew. Chem. 2009, 121, 2548-2551;
    • (2009) Angew. Chem. , vol.121 , pp. 2548-2551
    • Seidel, G.1    Mynott, R.2    Fürstner, A.3
  • 75
    • 70349778993 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 2510-2513;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2510-2513
  • 78
    • 53049098944 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 5030-5033. The nature of the substituents and the ancillary ligand determine the varying degrees of s and p bonding and the position of the gold species on a continuum from gold-stabilized singlet carbene to gold-stabilized carbocation. See:
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5030-5033
  • 81
    • 33744930835 scopus 로고    scopus 로고
    • b) C. Silva-Lpez, O. Nieto-Faza, R. Alvarez, A. R. de Lera, J. Org. Chem. 2006, 71, 4497-4501. We conducted a relaxed two-dimensional scan[26] starting from Va over the C3-C2′ and C3-C1′ coordinates, corresponding to the bond formation and bond cleavage involved in the indole migration. Figure 1 of the Supporting Information depicts the resulting potential energy surface for the transformation of Va into VIIa in a 3D plot. Although the study discards a concerted transformation, the stepwise process is clearly of low energy (see the Supporting Information).
    • (2006) J. Org. Chem. , vol.71 , pp. 4497-4501
    • Silva-Lpez, C.1    Nieto-Faza, O.2    Alvarez, R.3    De Lera, A.R.4
  • 84
    • 77955898124 scopus 로고    scopus 로고
    • A gold-Nazarov pathway similar to that of VIIa would involve the terminal phenyl group originating from the alternative structure with syn coordination of the gold catalyst to the indole ring. The Supporting Information includes the syn coordination manifold, which is non-competitive with the one shown in Figure 1
    • A gold-Nazarov pathway similar to that of VIIa would involve the terminal phenyl group originating from the alternative structure with syn coordination of the gold catalyst to the indole ring. The Supporting Information includes the syn coordination manifold, which is non-competitive with the one shown in Figure 1.
  • 85
    • 77955873921 scopus 로고    scopus 로고
    • Prepared from indole 1r by lithiation with nBuLi in THF and further treatment with the corresponding electrophile (diphenyl disulfide and ethyl chloroformate). See the Supporting Information
    • Prepared from indole 1r by lithiation with nBuLi in THF and further treatment with the corresponding electrophile (diphenyl disulfide and ethyl chloroformate). See the Supporting Information.
  • 86
    • 22244492360 scopus 로고    scopus 로고
    • For some selected examples of intramolecular hydroalkoxylation reactions of alkyne derivatives catalyzed by p-acid metallic species, see: a) S. Antoniotti, E. Genin, V. Michelet, J.-P Genpt, J. Am. Chem. Soc. 2005, 127, 9976 - 9977;
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 9976-9977
    • Antoniotti, S.1    Genin, E.2    Michelet, V.3    Genpt, J.-P.4
  • 88
    • 33745661090 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 2091-2093;
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2091-2093
  • 92
  • 96
    • 60749097519 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 1644-1647;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1644-1647
  • 99
    • 77955882325 scopus 로고    scopus 로고
    • See ref. [3c]
    • See ref. [3c].
  • 102
    • 34347335758 scopus 로고    scopus 로고
    • b) A. M. Walji, D. W. C. McMillan, Synlett 2007, 1477-1489. For some examples of concurrent tandem Brønsted acid-/metal-catalysis, see:
    • (2007) Synlett , pp. 1477-1489
    • Walji, A.M.1    McMillan, D.W.C.2
  • 105
    • 54749131823 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7044-7047.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7044-7047
  • 106
    • 77955861644 scopus 로고    scopus 로고
    • No more than 1 equiv of starting alkynol should be used for the alkylation step as we have observed that an excess of the propargylic alcohol has a deleterious effect on the gold catalysis
    • No more than 1 equiv of starting alkynol should be used for the alkylation step as we have observed that an excess of the propargylic alcohol has a deleterious effect on the gold catalysis.


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