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  • Title: Diastereo- and enantioselective conjugate addition of 3-substituted oxindoles to nitroolefins catalyzed by a chiral Ni(OAc)2-diamine complex under mild conditions.
    Author: Han YY, Wu ZJ, Chen WB, Du XL, Zhang XM, Yuan WC.
    Journal: Org Lett; 2011 Oct 07; 13(19):5064-7. PubMed ID: 21879728.
    Abstract:
    A simple catalyst system assembled from an enantiomerically pure diamine ligand and Ni(OAc)(2) efficiently generates chiral metal enolates derived from 3-substituted oxindoles bearing an N-1 carbonyl group. The enolates smoothly undergo diastereo- and enantioselective conjugate addition to a wide range of nitroolefins under mild reaction conditions, furnishing 3,3-disubstituted oxindole products bearing two vicinal quaternary/tertiary stereocenters in 74-95% yields and 60:40 to 99:1 dr, 71-97% ee.
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