4.8 Article

Conjugate Addition of 1,3-Dicarbonyl Compounds to Maleimides Using a Chiral C2-Symmetric Bis(2-aminobenzimidazole) as Recyclable Organocatalyst

Journal

ORGANIC LETTERS
Volume 13, Issue 22, Pages 6106-6109

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202599h

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Funding

  1. MEC [CTQ2007-62771/BQU, CTQ2010-20387, CSD2007-00006]
  2. Generalitat Valenciana [GV/2007/142, PROMETEO/2009/038]
  3. University of Alicante
  4. EU [CM0905]

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The recyclable chiral 2-aminobenzimidazole-derived organocatalyst if efficiently promotes the room temperature asymmetric conjugate addition of 1,3-diketones, beta-ketoesters, and malonates to maleimide and N-substituted maleimides, affording the corresponding Michael adducts in excellent yields and enantioselectivities even at gram scale.

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