4.5 Article

Highly Enantioselective Construction of Spirocyclopentaneoxindoles Containing Four Consecutive Stereocenters through an Organocatalytic Iminium-Enamine Cascade Reaction

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 24, Pages 5139-5143

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402687

Keywords

Organocatalysis; Asymmetric synthesis; Spiro compounds; Domino reactions; Michael addition

Funding

  1. National Basic Research Program of China (973 Program) [2010CB833300]
  2. Science and Technology of Hunan Province, China [2012FJ3023]

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Spirocyclopentaneoxindole derivatives containing four consecutive stereocenters, including a spiro quaternary center, were constructed by an organocatalytic iminium-enamine cascade sequence in good yields (up to 86%) with excellent enantiomeric (up to >99% ee) and diastereomeric purities (up to >99:1dr). This highly efficient procedure will allow diversity-oriented syntheses of this intriguing class of compounds with potential biological activities.

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