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Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives

An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experim...

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Hauptverfasser: Yamada, Tsuyoshi (VerfasserIn) , Park, Kwihwan (VerfasserIn) , Tachikawa, Takumu (VerfasserIn) , Fujii, Akiko (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn) , Sajiki, Hironao (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: [2020]
In: Organic letters
Year: 2020, Jahrgang: 22, Heft: 5, Pages: 1883-1888
ISSN:1523-7052
DOI:10.1021/acs.orglett.0c00221
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.0c00221
Volltext
Verfasserangaben:Tsuyoshi Yamada, Kwihwan Park, Takumu Tachikawa, Akiko Fujii, Matthias Rudolph, A. Stephen K. Hashmi, and Hironao Sajiki
Beschreibung
Zusammenfassung:An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.
Beschreibung:Gesehen am 20.04.2020
Beschreibung:Online Resource
ISSN:1523-7052
DOI:10.1021/acs.orglett.0c00221

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