Asymmetric Organocatalytic Cascade Synthesis of Tetrahydro-furanyl Spirooxindoles

Dmitri Trubitsõn, Sergei Žari, Sandra Kaabel, Marina Kudrjashova, Kadri Kriis, Ivar Järving, Tõnis Pehk*, Tõnis Kanger

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

8 Citations (Scopus)

Abstract

An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.

Original languageEnglish
Pages (from-to)314-322
Number of pages9
JournalSynthesis (Germany)
Volume50
Issue number2
DOIs
Publication statusPublished - 18 Jan 2018
MoE publication typeA1 Journal article-refereed

Keywords

  • domino reaction
  • enantioselectivity
  • heterocycles
  • Michael addition
  • organocatalysis

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