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Volumn , Issue 28, 2007, Pages 4635-4637

Fluorous synthesis of yuehchukene by α-lithiation of perfluoroalkyl-tagged 1-(arylsulfonyl)indole with mesityllithium

Author keywords

Fluorous solid phase extraction; Fluorous tags; Indole alkaloids; Lithiation; Yuehchukene

Indexed keywords


EID: 35348850936     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700525     Document Type: Article
Times cited : (25)

References (31)
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    • Review: a
    • Review: a) W. Zhang, Chem. Rev. 2004, 104, 2531;
    • (2004) Chem. Rev , vol.104 , pp. 2531
    • Zhang, W.1
  • 13
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    • Most of the typical fluorous tags require methylene spacers between the perfluoroalkyl chains and the tagging functionalities to reduce the influence of the perfluorated moieties. When molecules with these tags are exposed to typical lithiation conditions, undesired deprotonation of acidic protons on the methylene spacers occurs as a problematic side reaction, Chemical Equation Presented
    • Most of the typical fluorous tags require methylene spacers between the perfluoroalkyl chains and the tagging functionalities to reduce the influence of the perfluorated moieties. When molecules with these tags are exposed to typical lithiation conditions, undesired deprotonation of acidic protons on the methylene spacers occurs as a problematic side reaction. (Chemical Equation Presented)
  • 14
    • 0035135768 scopus 로고    scopus 로고
    • 3-(Perfluorooctyl)benzenesulfonyl chloride: S. Cerezo, J. Cortes, D. Galvan, E. Lago, C. Marchi, E. Molins, M. Moreno-Manas, R. Pleixats, J. Torrejon, A. Vallribera, Eur. J. Org. Chem. 2001, 329.
    • 3-(Perfluorooctyl)benzenesulfonyl chloride: S. Cerezo, J. Cortes, D. Galvan, E. Lago, C. Marchi, E. Molins, M. Moreno-Manas, R. Pleixats, J. Torrejon, A. Vallribera, Eur. J. Org. Chem. 2001, 329.
  • 19
    • 35348917229 scopus 로고    scopus 로고
    • Other metallic bases were also tested, but MesLi in diethyl ether was proved to be the best reagent for our purpose; see Supporting Information for details
    • Other metallic bases were also tested, but MesLi in diethyl ether was proved to be the best reagent for our purpose; see Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.