Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones

Mamatha Amireddy, Kwunmin Chen

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20:1 dr and 86% ee).

Original languageEnglish
Pages (from-to)8003-8008
Number of pages6
JournalTetrahedron
Volume71
Issue number42
DOIs
Publication statusPublished - 2015 Oct 21

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Keywords

  • 2-Arylideneindane-1 3-diones
  • Cascade reaction
  • Michael-aldol
  • Squaramide-catalyst
  • γ-Nitro ketones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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