Synfacts 2006(3): 0251-0251  
DOI: 10.1055/s-2006-932019
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Regio- and Enantioselective Allylation of Ketone Enolates

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Graening, J. F. Hartwig*
Yale University, New Haven, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

Using the described method, the authors overcome many problems often associated with the alkylation of unstabilized ketone enolates and achieve high reactivity, regioselectivity and enantioselectivity for a wide class of substrates. The key for this reaction was the addition of a combination of fluoride sources (CsF and ZnF2) that enable the reaction to proceed with high reactivity and selectivity. Without the fluoride source, the reaction did not proceed at all.