Kinetic Zn-Enolate Formation by Reaction of CH2(ZnI)2 with a Thiol Ester

Z. Ikeda; T. Hirayama; S. Matsubara

doi:10.1055/s-2006-955853

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Synfacts 2007(2): 0173-0173
DOI: 10.1055/s-2006-955853

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Kinetic Zn-Enolate Formation by Reaction of CH₂(ZnI)₂ with a Thiol Ester

Contributor(s): Mark Lautens, Yann Béthuel
Z. Ikeda, T. Hirayama, S. Matsubara*
Kyoto University, Japan

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Publication History

Publication Date:
23 January 2007 (online)

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Significance

The unique behavior of bis(iodozincio)methane towards electrophiles (two nucleophilic sites, see book below) combined with the mildness of organozinc reagents allowed for the chemo- and regioselective synthesis of kinetic enolates by reaction with thiol esters under palladium catalysis.