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  • Title: Dual organocatalysis: asymmetric allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates.
    Author: Cui HL, Peng J, Feng X, Du W, Jiang K, Chen YC.
    Journal: Chemistry; 2009; 15(7):1574-7. PubMed ID: 19132709.
    Abstract:
    The first highly enantioselective allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates by dual catalysis of (DHQD)(2)AQN and (S)-BINOL has been investigated. Excellent stereoselectivities have been achieved for a broad spectrum of substrates (d.r. > 99:1, up to 99 % ee). The multifunctional allylic products could be efficiently converted to a range of complex chiral cyclic frameworks. EWG = electron-withdrawing group, (DHQD)(2)AQN = hydroquinidine (anthraquinone-1,4-diyl) diether, (S)-BINOL = (S)-(-)-1,1'-bi-2-naphthol.
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