DMAP-Catalyzed Efficient Diastereo- and Regioselective Synthesis of Isoxazolone-Based Bisspiroheterocyclic Oxindoles

Rong Rong Zhu, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A strategic approach to incorporate CF3 group into oxindoles, pyrrolidines, and isoxazolones to construct spiro heterocyclic skeletons with quaternary carbon stereocenters was developed. Using a DMAP catalyst under mild conditions, the controllable synthesis of spiro oxindole-pyrrolidine-isoxazoline derivatives was achieved via concerted 1,3-dipolar cycloaddition reactions of arylidene isoxazolones with N-(2,2,2-trifluoroethyl)isatin ketimines. This method exhibits robust regioselectivity and provides a series of isoxazolone-based bispiro heterocycles in good to high yields (72 %–99 %) with excellent diastereoselectivity (in all cases >20 : 1 dr), offering new candidate compounds for drug screen.

Original languageEnglish
Article numbere202400959
JournalEuropean Journal of Organic Chemistry
Volume27
Issue number48
DOIs
Publication statusPublished - 23 Dec 2024

Keywords

  • 1,3-dipolar cycloaddition
  • Isatin ketimines
  • Isoxazolones
  • Oxindoles
  • Spiroheterocycles

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