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Josiphos-Catalyzed Asymmetric Homodimerization of Ketoketenes

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journal contribution
posted on 19.11.2010, 00:00 by Ahmad A. Ibrahim, Pei-Hsun Wei, Gero D. Harzmann, Nessan J. Kerrigan
In this paper the development of a chiral phosphine-catalyzed homodimerization of ketoketenes that provides access to a variety of highly substituted ketoketene dimer β-lactones (11 examples) is reported. The Josiphos catalytic system displays good to excellent enantioselectivity (up to 96% ee). Ring-opening reactions of the enantioenriched ketoketene dimers were also carried out to access 1,3-diketones, enol esters, and β-hydroxyketones with good diastereoselectivity.