Squaramide-Catalyzed Asymmetric Michael/Cyclization Cascade Reaction of Unsaturated Thiazolidinones and 3-Isothiocyanato Oxindoles: Synthesis of New Bispirocyclic Heterocycles

Yong Xing Song, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

A highly efficient method for the construction of oxindole-pyrrolidone-thiazolidinone bispirocyclic heterocycles bearing three contiguous chiral centers including two quaternary one via a Michael/cyclization cascade reaction has been developed. Using bifunctional cinchona-derived squaramide as catalyst, the reactions of 3-isothiocyanato oxindoles with unsaturated thiazolidinone derivatives proceeded smoothly under mild reaction conditions to afford a series of complex chiral oxindole-pyrrolidone-thiazolidinone bispirocyclic heterocycles in high yields (up to 99%) with excellent diastereo- and enantioselectivities (up to >99:1 dr, >99% ee).

Original languageEnglish
Pages (from-to)1535-1545
Number of pages11
JournalSynthesis
Volume50
Issue number7
DOIs
Publication statusPublished - 3 Apr 2018

Keywords

  • 3-isothiocyanato oxindoles
  • Michael/cyclization cascade reaction
  • asymmetric catalysis
  • organocatalysis
  • thiazolidinone derivatives

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Song, Y. X., & Du, D. M. (2018). Squaramide-Catalyzed Asymmetric Michael/Cyclization Cascade Reaction of Unsaturated Thiazolidinones and 3-Isothiocyanato Oxindoles: Synthesis of New Bispirocyclic Heterocycles. Synthesis, 50(7), 1535-1545. https://doi.org/10.1055/s-0036-1591527