Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones: En route to 3,2′-pyrrolidinyl bispirooxindoles

Satavisha Kayal, Santanu Mukherjee

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

Cascade Michael/cyclization reactions between 3-isothiocyanato oxindoles and exocyclic α,β-unsaturated ketones are shown to proceed efficiently in the presence of a quinine-derived tertiary amino-squaramide catalyst and furnish 3,2′-pyrrolidinyl bispirooxindoles containing two spiro-quaternary and three contiguous stereocenters as a single diastereomer with excellent enantioselectivities (up to 99:1 er).

Original languageEnglish
Pages (from-to)10175-10179
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number43
DOIs
Publication statusPublished - 2016 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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