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  • Title: Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates.
    Author: Yang W, Tan D, Li L, Han Z, Yan L, Huang KW, Tan CH, Jiang Z.
    Journal: J Org Chem; 2012 Aug 03; 77(15):6600-7. PubMed ID: 22816444.
    Abstract:
    The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity.
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