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Gold-Catalyzed Deoxygenative Nazarov Cyclization of 2,4-Dien-1-als for Stereoselective Synthesis of Highly Substituted Cyclopentenes

Lin, Chung-Chang ; Teng, Tse-Min ; Tsai, Chung-Chih ; Liao, Hsin-Yi ; Liu, Rai-Shung

Journal of the American Chemical Society, 2008-12, Vol.130 (48), p.16417-16423 [Periódico revisado por pares]

United States: American Chemical Society

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  • Título:
    Gold-Catalyzed Deoxygenative Nazarov Cyclization of 2,4-Dien-1-als for Stereoselective Synthesis of Highly Substituted Cyclopentenes
  • Autor: Lin, Chung-Chang ; Teng, Tse-Min ; Tsai, Chung-Chih ; Liao, Hsin-Yi ; Liu, Rai-Shung
  • É parte de: Journal of the American Chemical Society, 2008-12, Vol.130 (48), p.16417-16423
  • Notas: ark:/67375/TPS-N9C5D10K-S
    istex:C8AAAA802FC4C2F0751CE898185763424B4B3C4D
    Tables S1−S3, experimental procedures for synthesis of cis-2,4-dien-1-al substrates and catalytic operations, NMR spectra, and spectral data of new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.
    ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Treatment of 2,4-dien-1-als with allylsilanes and PPh3AuSbF6 (3 mol %) led to formation of 1,4-bis(allyl)cyclopentenyl products; this gold catalyst is superior to commonly used Lewis acids according to catalyst screening. Such gold-catalyzed deoxygenative cyclizations are compatible with various oxygen-, amine-, sulfur-, hydrogen-, and carbon-based nucleophiles. The value of this new catalysis is demonstrated by the diverse annulations of 2,4-dien-1-als with electron-rich alkenes and arenes, providing an easy access to complicated cyclopentenyl frameworks. Structural analysis of annulation products reveals evidence for the participation of Nazarov cyclization. This deoxygenative cyclization is extensible to a tandem intramolecular cyclization/nucleophilic addition cascade, giving polycyclic carbo- or oxacyclic compounds with controlled stereochemistry. This new gold catalysis is applied to a short synthesis of natural compounds of the brazilane family, including brazilane, O-trimethyl-, and O-tetramethyl brazilane.
  • Editor: United States: American Chemical Society
  • Idioma: Inglês
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