4.7 Article

Bicyclic guanidine-catalyzed asymmetric Michael additions of 3-benzyl-substituted oxindoles to N-maleimides

Journal

CHEMICAL COMMUNICATIONS
Volume 48, Issue 42, Pages 5124-5126

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cc31587d

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Funding

  1. NSFC [21072044]
  2. Excellent Youth Foundation of Henan Scientific Committee [114100510003]
  3. International Cooperation Foundation of Henan Province [104300510062]
  4. NUS ARF [R-143-000-461-112]

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A bicyclic guanidine-catalyzed Michael addition of 3-benzyl substituted oxindoles to N-maleimides has been developed to produce oxindole derivatives with a quaternary carbon chiral center at the 3-position in excellent yields and enantio- and diastereoselectivities. This is the first incorporation of N-benzylic alpha-branched succinimides into 3,3-disubstituted oxindoles.

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