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Volumn 11, Issue 11, 2009, Pages 2293-2296

Counterion effects in a gold-catalyzed synthesis of pyrroles from alkynyl aziridines

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EID: 66149185302     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900609f     Document Type: Article
Times cited : (157)

References (46)
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    • For a discussion and review of π-acid alkyne activation by platinum and gold see: Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
  • 2
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    • For selected recent reviews of gold catalysis
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    • Chem. Re , vol.2008 , Issue.108 , pp. 3351
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  • 11
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    • For a recent report exploring the position and effect of counterion on alkene-cationic gold fragments, see: Zuccaccia, D, Belpassi, L, Tarantelli, F, Macchione, A. J. Am. Chem. Soc. 2009, 31, 3170
    • For a recent report exploring the position and effect of counterion on alkene-cationic gold fragments, see: Zuccaccia, D.; Belpassi, L.; Tarantelli, F.; Macchione, A. J. Am. Chem. Soc. 2009, 31, 3170.
  • 22
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    • For selected reviews of heterocycle synthesis by gold, see
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    • Patil, N.1    Yamamoto, Y.2
  • 27
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    • For examples of gold-catalyzed pyrrole synthesis, see: Witham, C. A, Mauleon, P, Shapiro, N. D, Sherry, B. D, Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838
    • For examples of gold-catalyzed pyrrole synthesis, see: Witham, C. A.; Mauleon, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
  • 37
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    • Throughout this study, the aziridines were used as mixtures of the cis- and trans-diastereomers, with the cis-diastereomer predominant. See Supporting Information for ratios.
    • Throughout this study, the aziridines were used as mixtures of the cis- and trans-diastereomers, with the cis-diastereomer predominant. See Supporting Information for ratios.
  • 38
    • 66149172074 scopus 로고    scopus 로고
    • 1D GOESY (NOE) experiments confirm the regiochemistry within 6a (see Supporting Information).
    • 1D GOESY (NOE) experiments confirm the regiochemistry within 6a (see Supporting Information).
  • 39
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    • The use of the 4-methoxyphenyl substituent led to degradation of the starting material
    • The use of the 4-methoxyphenyl substituent led to degradation of the starting material.
  • 40
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    • An alternative analysis is that close association of a Lewis basic counterion or solvent to the cation may disfavor or block the orbital alignment required for the 1,2-aryl shift to take place
    • An alternative analysis is that close association of a Lewis basic counterion or solvent to the cation may disfavor or block the orbital alignment required for the 1,2-aryl shift to take place.
  • 41
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    • For examples of 1,2-alkyl and aryl shifts in gold-catalyzed reactions see, ref 13d and Kirsch, S. F, Binder, J. T, Lie'bert, C, Menz, H. Angew. Chem, Int. Ed. 2006, 45, 5878
    • For examples of 1,2-alkyl and aryl shifts in gold-catalyzed reactions see, ref 13d and Kirsch, S. F.; Binder, J. T.; Lie'bert, C.; Menz, H. Angew. Chem., Int. Ed. 2006, 45, 5878.
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    • Crone, B.; Kirsch, S. F. Chem.sEur. J. 2008, 14, 3514.
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  • 46
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    • For a theoretical investigation into the role of a triflate counterion in the proton-transfer step of gold-catalyzed hydroamination of alkenes, see: Kova'cs, G, Ujaque, G, Lledo's, A. J. Am. Chem. Soc. 2008, 130, 853
    • For a theoretical investigation into the role of a triflate counterion in the proton-transfer step of gold-catalyzed hydroamination of alkenes, see: Kova'cs, G.; Ujaque, G.; Lledo's, A. J. Am. Chem. Soc. 2008, 130, 853.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.