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  • Title: Enantioselective formation of cyano-bearing all-carbon quaternary stereocenters: desymmetrization by copper-catalyzed N-arylation.
    Author: Zhou F, Cheng GJ, Yang W, Long Y, Zhang S, Wu YD, Zhang X, Cai Q.
    Journal: Angew Chem Int Ed Engl; 2014 Sep 01; 53(36):9555-9. PubMed ID: 25045110.
    Abstract:
    The enantioselective construction of all-carbon quaternary stereocenters is one of the most challenging fields in asymmetric synthesis. An asymmetric desymmetrization strategy offers an indirect and efficient method for the formation of all-carbon stereocenters. An enantioselective formation of cyano-bearing all-carbon quaternary stereocenters in 1,2,3,4,-tetrahydroquinolines and 2,3,4,5-tetrahydro-1H-benzo[b]azepines by copper-catalyzed desymmetric N-arylation is demonstrated. The cyano group at the prochiral center plays a key role for the high enantioselectivity and works as an important functional group for further transformations. DFT studies provide a model which successfully accounts for the origin of enantioselectivity.
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