Novel Method for Synthesizing Spiro[4.5]cyclohexadienones through a Pd-Catalyzed Intramolecular ipso-Friedel−Crafts Allylic Alkylation of Phenols

Novel Method for Synthesizing Spiro[4.5]cyclohexadienones through a Pd-Catalyzed Intramolecular ipso-Friedel−Crafts Allylic Alkylation of Phenols

The first successful Pd-catalyzed intramolecular ipso-Friedel−Crafts allylic alkylation of phenols, which provided a new access to spiro[4.5]cyclohexadienones, is described. The present method could be applied to catalytic enantioselective construction of an all-carbon quaternary spirocenter.

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Veröffentlicht in:Organic letters 2010-11, Vol.12 (21), p.5020-5023
Hauptverfasser: Nemoto, Tetsuhiro, Ishige, Yuta, Yoshida, Mariko, Kohno, Yuta, Kanematsu, Mutsumi, Hamada, Yasumasa
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Catalysis
Cyclohexenes - chemical synthesis
Molecular Structure
Palladium - chemistry
Phenols - chemistry
Spiro Compounds - chemical synthesis
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Zusammenfassung:The first successful Pd-catalyzed intramolecular ipso-Friedel−Crafts allylic alkylation of phenols, which provided a new access to spiro[4.5]cyclohexadienones, is described. The present method could be applied to catalytic enantioselective construction of an all-carbon quaternary spirocenter.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102190s