Enantioselective synthesis of enol lactones from tandem Michael addition/lactonization catalyzed by a chiral squaramide catalyst

The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with α,β-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 25; no. 4; pp. 310 - 317
Main Authors Zhao, Bo-Liang, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.02.2014
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
PHENOLS
ACID
INHIBITORS
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Summary:The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with α,β-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good yields with moderate to high enantioselectivities (up to 88% ee) through the enantioselective Michael addition followed by lactonization and removal of the succinimide auxiliary.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2014.01.005