Asymmetric organocatalytic aza-michael reactions of isatin derivatives

Sergei Žari, Andrus Metsala, Marina Kudrjashova, Sandra Kaabel, Ivar Järving, Tõnis Kanger*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

14 Citations (Scopus)

Abstract

Isatin was activated by derivatization to a Schiff base with aniline and used as an aza-Michael donor in organocatalytic asymmetric reactions with symmetric and nonsymmetric unsaturated 1,4-diketones. After hydrolysis (in situ), the N-substituted isatins were obtained in high yields (up to >95%) with high enantioselectivity (up to 95%).

Original languageEnglish
Pages (from-to)875-886
Number of pages12
JournalSynthesis (Germany)
Volume47
Issue number6
DOIs
Publication statusPublished - Mar 2015
MoE publication typeA1 Journal article-refereed

Keywords

  • asymmetric catalysis
  • chemoselectivity
  • enantioselectivity
  • imines
  • Michael addition

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