4.0 Article

Asymmetric synthesis of multicyclic spiro-1,3-indandiones via a cascade Michael/Michael reaction of curcumins and 2-arylidene-1,3-indandiones

Journal

TETRAHEDRON-ASYMMETRY
Volume 24, Issue 7, Pages 402-408

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2013.02.014

Keywords

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Funding

  1. National Natural Science Foundation of China [20972195, 21172270, 21202208]
  2. Guangdong Engineering Research Center of Chiral Drugs

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An organocatalytic cascade Michael/Michael reaction between curcumins and 2-arylidene-1,3-indandiones has been studied. Prolinol, chiral thiourea-tertiary amines, and cinchona alkaloids were evaluated as catalysts. Quinine was identified as the best catalyst for the transformation. Multicyclic spiro-1,3-indandiones were prepared in moderate to excellent yields, diastereoselectivities, and enantioselectivities. (c) 2013 Elsevier Ltd. All rights reserved.

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