Catalytic Asymmetric Michael Addition/Cyclization Cascade Reaction of 3-Isothiocyanatooxindoles with Nitro Olefins

Satavisha Kayal, Santanu Mukherjee

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

The first organocatalytic asymmetric reaction of 3-isothiocyanatooxindoles with nitro olefins has been developed by using a cinchonidine-derived bifunctional catalyst. The resulting products, highly functionalized 3,2′-pyrrolidinyl-substituted spirooxindole derivatives, were obtained in high yields with good diastereo- and enantioselectivities (up to dr >20:1 and er = 96:4). This Michael addition/cyclization cascade reaction employs monosubstituted nitro olefins and complements the ZnII-catalyzed variant, which is only applicable to disubstituted nitro olefins. The first organocatalytic asymmetric reaction of 3-isothiocyanatooxindoles with nitro olefins has been developed by using a cinchonidine-derived bifunctional catalyst. The resulting products, highly functionalized 3,2′-pyrrolidinyl spirooxindole derivatives, were obtained in high yields with good diastereo- and enantioselectivities (dr up to >20:1 and er = 96:4).

Original languageEnglish
Pages (from-to)6696-6700
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number30
DOIs
Publication statusPublished - 2014 Oct 1
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Cascade reactions
  • Michael addition
  • Nitrogen heterocycles
  • Spiro compounds

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Catalytic Asymmetric Michael Addition/Cyclization Cascade Reaction of 3-Isothiocyanatooxindoles with Nitro Olefins'. Together they form a unique fingerprint.

Cite this