Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
J Org Chem. 2010 Nov 19;75(22):7901-4. doi: 10.1021/jo101867m. Epub 2010 Oct 29.
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.
本文报道了一种手性膦催化酮烯酮的同二聚反应，该反应可得到多种高取代的酮烯酮二聚体β-内酰胺（11 个实例）。Josiphos 催化体系表现出良好到优异的对映选择性（高达 96%ee）。对富集对映体的酮烯酮二聚体进行开环反应，也可得到 1,3-二酮、烯醇酯和β-羟基酮，具有良好的非对映选择性。
