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  • Title: Organocatalytic asymmetric Michael-type/Wittig reaction of phosphorus ylides: synthesis of chiral α-methylene-δ-ketoesters.
    Author: Lin A, Wang J, Mao H, Ge H, Tan R, Zhu C, Cheng Y.
    Journal: Org Lett; 2011 Aug 19; 13(16):4176-9. PubMed ID: 21755912.
    Abstract:
    An asymmetric Michael-type reaction of phosphorus ylides and α,β-unsaturated ketones under the catalysis of a chiral ion pair catalyst has been described. The ion pair catalyst containing a chiral counteranion was prepared by simply mixing 9-amino-(9-deoxy)-epi-quinine with l-N-Boc-proline. The optically active α-methylene-δ-ketoesters could be obtained with good to excellent enantioselectivities (up to 95% ee) under mild reaction conditions.
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