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Accessing Medium-Sized Rings via Vinyl Carbocation Intermediates.
Zhao, Zhenqi; Popov, Stasik; Lee, Woojin; Burch, Jessica E; Delgadillo, David A; Kim, Lee Joon; Shahgholi, Mona; Lebrón-Acosta, Naiara; Houk, K N; Nelson, Hosea M.
Afiliación
  • Zhao Z; Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Popov S; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
  • Lee W; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
  • Burch JE; Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Delgadillo DA; Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Kim LJ; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
  • Shahgholi M; Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Lebrón-Acosta N; Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Houk KN; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
  • Nelson HM; Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Org Lett ; 26(5): 1000-1005, 2024 Feb 09.
Article en En | MEDLINE | ID: mdl-38295154
ABSTRACT
Medium-sized rings (8-11-membered cycles) are often more challenging to synthesize than smaller rings (5-7-membered cycles) due to ring strain. Herein, we report a catalytic method for forming 8- and 9-membered rings that proceeds via the intramolecular Friedel-Crafts reactions of vinyl carbocation intermediates. These reactive species are generated catalytically through the ionization of vinyl toluenesulfonates by a Lewis acidic lithium cation-weakly coordinating anion salt.
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Año: 2024 Tipo del documento: Article
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Año: 2024 Tipo del documento: Article