Asymmetric Organocatalytic Michael Addition-Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

Gert Preegel, Estelle Silm, Sandra Kaabel, Ivar Järving, Kari Rissanen, Margus Lopp*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)

Abstract

An asymmetric organocatalytic Michael addition-cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and α,β-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.

Original languageEnglish
Pages (from-to)3118-3125
Number of pages8
JournalSynthesis (Germany)
Volume49
Issue number14
DOIs
Publication statusPublished - 17 Jul 2017
MoE publication typeA1 Journal article-refereed

Keywords

  • asymmetry
  • dihydropyran
  • diketones
  • Michael addition
  • organocatalysis

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