Highly Diastereo- And Enantioselective Synthesis of Isoxazolone-Spirooxindoles via Squaramide-Catalyzed Cascade Michael/Michael Addition Reactions

Yu Wang, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A highly enantioselective [3+2] annulation of 3-((2-oxoindolin-3-yl)oxy)acrylates with isoxazol-5(4H)-ones has been accomplished by squaramide-catalyzed cascade Michael/Michael addition reactions under mild conditions. The corresponding isoxazolone-spirooxindoles with four continuous stereocenters were obtained in moderate to high yields with excellent stereoselectivities (up to >20:1 dr, 97% ee). The synthetic practicality of this methodology was illustrated by performing the reaction on a gram scale with the same efficiency and stereoselectivity. Meanwhile, the isoxazol-5(4H)-one ring could be opened by the reaction with iron powder and ammonium chloride, and the corresponding acyl derivative can be obtained with a maintained yield and stereoselectivity.

Original languageEnglish
Pages (from-to)15325-15336
Number of pages12
JournalJournal of Organic Chemistry
Volume85
Issue number23
DOIs
Publication statusPublished - 4 Dec 2020

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