Indium-Catalyzed Homo-Nazarov Cyclizations of Alkenyl Cyclopropyl Ketones

Herein, an efficient Lewis acid catalyzed protocol for the homo-Nazarov cyclizations of alkenyl cyclopropyl ketones is reported. Alkenes bearing β-hydrogens (or silyl groups) provide 1.5:1 mixtures of methylene cyclohexenols and cyclohexenones. When no β-hydrogens (or silyl groups) are present, only...

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Bibliographic Details
Published in:Organic letters 2010-12, Vol.12 (24), p.5684-5687
Main Authors: Patil, Dadasaheb V, Phun, Lien H, France, Stefan
Format: Article
Language:English
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Summary:Herein, an efficient Lewis acid catalyzed protocol for the homo-Nazarov cyclizations of alkenyl cyclopropyl ketones is reported. Alkenes bearing β-hydrogens (or silyl groups) provide 1.5:1 mixtures of methylene cyclohexenols and cyclohexenones. When no β-hydrogens (or silyl groups) are present, only cyclohexenones are observed. Products are rapidly formed in good to high yields (up to 93%) under mild conditions and could be readily derivatized.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102497w