Gold-Catalyzed Stereocontrolled Oxacyclization/[4+2]-Cycloaddition Cascade of Ketone-Allene Substrates

Gold-Catalyzed Stereocontrolled Oxacyclization/[4+2]-Cycloaddition Cascade of Ketone-Allene Substrates

We report the first success on the Au-catalyzed tandem oxacyclization/[4+2]-cycloaddition cascade using ketone-allene substrates to give highly substituted oxacyclics with excellent stereocontrol. In contrast to oxo-alkyne substrates, the resulting cycloadducts are isolable and efficiently produced...

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Veröffentlicht in:Journal of the American Chemical Society 2010-07, Vol.132 (27), p.9298-9300
Hauptverfasser: Teng, Tse-Min, Liu, Rai-Shung
Format: Artikel
Sprache:eng
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Zusammenfassung:We report the first success on the Au-catalyzed tandem oxacyclization/[4+2]-cycloaddition cascade using ketone-allene substrates to give highly substituted oxacyclics with excellent stereocontrol. In contrast to oxo-alkyne substrates, the resulting cycloadducts are isolable and efficiently produced from a reasonable scope of enol ethers.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja1043837