Squaramide-Catalyzed Enantioselective Cascade Approach to Bispirooxindoles with Multiple Stereocenters

Bo Liang Zhao, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of spirotetrahydrofuran bispirooxindoles was developed. The products were obtained in moderate to excellent yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, >99% ee). This straightforward process serves as a powerful method for the enantioselective construction of potentially bioactive bispirooxindoles in which two of the four contiguous chiral centers are spiro all-carbon quaternary centers on a single tetrahydrofuran ring. Meanwhile, the synthetic practicality of this methodology was illustrated by performing the reaction on a gram-scale with the same efficiency and stereoselectivity. (Figure presented.).

Original languageEnglish
Pages (from-to)3992-3998
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number24
DOIs
Publication statusPublished - 22 Dec 2016

Keywords

  • Michael addition
  • asymmetric catalysis
  • organocatalysis
  • spirooxindoles
  • squaramides

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Zhao, B. L., & Du, D. M. (2016). Squaramide-Catalyzed Enantioselective Cascade Approach to Bispirooxindoles with Multiple Stereocenters. Advanced Synthesis and Catalysis, 358(24), 3992-3998. https://doi.org/10.1002/adsc.201600782