Asymmetric proline-catalyzed addition of aldehydes to 3H-indol-3-ones: Enantioselective synthesis of 2,3-dihydro-1H-indol-3-ones with quaternary stereogenic centers

Magnus Rueping*, Ramesh Rasappan, Sadiya Raja

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

The proline-catalyzed addition of various aliphatic aldehydes to sterically hindered 2-aryl-substituted 3H-indol-3-ones affords 2,2-disubstituted 2,3-dihydro-1H-indol-3-one derivatives with excellent enantioselectivities. In addition, the synthesis of a chiral derivative, (S)-2-(2-bromophenyl)-2,3- dihydro-2-(2-hydroxyethyl)-1H-indol-3-one, which can be used as an intermediate for the preparation of the natural product hinckdentine A was accomplished with a high level of enantioselectivity.

Original languageEnglish (US)
Pages (from-to)2296-2303
Number of pages8
JournalHelvetica Chimica Acta
Volume95
Issue number11
DOIs
StatePublished - Nov 1 2012

Keywords

  • Catalysis
  • Hinckdentine A
  • Indol-2-acetaldehyde
  • Mannich reaction
  • Proline

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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