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

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...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 24; no. 7; pp. 402 - 408
Main Authors Luo, Nian-hua, Sun, Xiang, Wei, Wen-tao, Zhang, Xue-jing, Yan, Ming
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.04.2013
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
MICHAEL REACTION
DIELS-ALDER
KNOEVENAGEL
ENANTIOSELECTIVE SYNTHESIS
NITROCYCLOPROPANES
ORGANOCATALYTIC CONJUGATE ADDITION
CONSTRUCTION
EFFICIENT SYNTHESIS
DERIVATIVES
NITROALKENES
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Summary: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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2013.02.014