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  • Title: Catalytic enantioselective alkylations of tetrasubstituted olefins. Synthesis of all-carbon quaternary stereogenic centers through Cu-catalyzed asymmetric conjugate additions of alkylzinc reagents to enones.
    Author: Hird AW, Hoveyda AH.
    Journal: J Am Chem Soc; 2005 Nov 02; 127(43):14988-9. PubMed ID: 16248613.
    Abstract:
    A method for Cu-catalyzed asymmetric conjugate addition (ACA) of dialkylzinc reagents to tetrasubstituted five- and six-membered cyclic enones that afford quaternary all-carbon stereogenic centers in up to 95% ee is reported. Catalytic ACAs are practical and efficient. Reactions proceed to >98% conversion in undistilled commercial grade toluene in the presence of 2 mol % of an air-stable Cu salt (CuCN) and a readily available chiral ligand. Enantioselective ACA reactions deliver products that can be readily functionalized to afford a variety of synthetically versatile compounds in high optical purity.
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