Organocatalytic formal [5+1] annulation: Diastereoselective cascade synthesis of functionalized six-membered spirocyclic indane-1,3-diones/oxindoles via Michael-aldol reaction

Suparna Roy, Mamatha Amireddy, Kwunmin Chen

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

An efficient cascade protocol has been developed for the diastereoselective synthesis of functionalized six-membered spirocyclic compounds. The reaction proceeded smoothly between indane 1,3-diones/oxindoles/coumaranone as the dinucleophilic components and (E)-5-nitro-6-aryl-hex-5-en-2-one as the dielectrophile to give the desired products with reasonable to high chemical yields (30-84%) and high levels of diastereoselectivities (upto >95:5 dr). The reaction proceeded smoothly via cascade Michael-aldol reaction.

Original languageEnglish
Pages (from-to)8751-8757
Number of pages7
JournalTetrahedron
Volume69
Issue number41
DOIs
Publication statusPublished - 2013 Oct 14

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3-hydroxybutanal
oxindole

Keywords

  • Cascade Michael-aldol Oxindole Diastereoselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Organocatalytic formal [5+1] annulation : Diastereoselective cascade synthesis of functionalized six-membered spirocyclic indane-1,3-diones/oxindoles via Michael-aldol reaction. / Roy, Suparna; Amireddy, Mamatha; Chen, Kwunmin.

In: Tetrahedron, Vol. 69, No. 41, 14.10.2013, p. 8751-8757.

Research output: Contribution to journalArticle

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