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Synfacts 2009(12): 1358-1358  
DOI: 10.1055/s-0029-1218236
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Scandium-Catalyzed Stereoselective Nazarov Reaction

Contributor(s): Hisashi Yamamoto, Zhi Li
K. Yaji, M. Shindo*
Kyushu University, Kasuga, Japan
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

The authors described an asymmetric version of the Nazarov reaction of monodentate ketone substrates. A quaternary chiral center was created in this reaction. An isotope-­labeling experiment indicated that the mechanism involved Lewis acid catalyzed cyclization and subsequent intermolecular nucleophilic attack of the alkoxy group at the α-position of the ketone.