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Madavi S Prasad1, Sankar Bharani1, Murugesan Sivaprakash1

  • 1Asymmetric synthesis and catalysis laboratory, Department of Chemistry, Central University of Tamil Nadu (CUTN), Tiruvarur-610 005, India. shivaprasad@cutn.ac.in.

Organic & Biomolecular Chemistry
|June 5, 2023
PubMed
Summary

This study introduces N-2,2,2-trifluoroethylisatin ketimine for asymmetric synthesis. It details the first organocatalyzed [3 + 2]-addition to create novel spirothiazolidine oxindoles with high selectivity.

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Medicinal Chemistry

Background:

  • Isatin derivatives are crucial scaffolds in medicinal chemistry.
  • Developing efficient asymmetric synthetic routes is vital for drug discovery.

Purpose of the Study:

  • To report the first use of N-2,2,2-trifluoroethylisatin ketimine as a 1,2-dipolarophile.
  • To achieve the first asymmetric synthesis of N-2,2,2-trifluoroethylspirothiazolidine oxindoles.
  • To explore the synthetic utility of the novel compounds.

Main Methods:

  • Organocatalyzed asymmetric [3 + 2]-addition reaction.
  • Utilizing N-2,2,2-trifluoroethylisatin ketimine and 1,4-dithiane-2,5-diol.
  • Purification and characterization of synthesized compounds.

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Main Results:

  • Successfully synthesized a diverse library of N-2,2,2-trifluoroethylspirothiazolidine oxindoles (up to 25 examples).
  • Achieved excellent yields (up to 96%) and high stereoselectivity (up to 99% ee, 99:1 dr).
  • Demonstrated the transformation of optically pure products into medicinally relevant derivatives.

Conclusions:

  • Established a novel and efficient method for asymmetric synthesis of trifluoroethylspirothiazolidine oxindoles.
  • The developed methodology offers access to valuable chiral building blocks for medicinal chemistry.
  • Highlights the potential of N-2,2,2-trifluoroethylisatin ketimine in complex molecule synthesis.