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  • Title: Nickel-Catalyzed Conjugate Addition of Silyl Ketene Imines to In Situ Generated Indol-2-ones: Highly Enantioselective Construction of Vicinal All-Carbon Quaternary Stereocenters.
    Author: Zheng J, Lin L, Dai L, Tang Q, Liu X, Feng X.
    Journal: Angew Chem Int Ed Engl; 2017 Oct 09; 56(42):13107-13111. PubMed ID: 28779506.
    Abstract:
    The first enantioselective conjugate addition of silyl ketene imines to in situ generated indol-2-ones was performed in the presence of a chiral N,N'-dioxide/NiII catalyst. This method provides efficient access to chiral β-alkyl nitriles bearing congested vicinal all-carbon quaternary stereocenters in up to 90 % yield with 23:1 d.r. and 98 % ee. The products enable facile transformations to chiral pyrroloindoline frameworks and spirocyclohexane oxindole derivatives. A possible transition state was also proposed to explain the origin of the asymmetric induction.
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