Asymmetric synthesis of spirooxindole-fused spirothiazolones via squaramide-catalysed reaction of 3-chlorooxindoles with 5-alkenyl thiazolones

Yong Xing Song, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

An efficient and practical organocatalyzed asymmetric formal [2 + 1] cycloaddition of 3-chlorooxindoles with 5-alkenyl thiazolones by using hydroquinine-derived squaramide as the catalyst has been developed. Under mild conditions, a broad range of spirooxindole-fused spirothiazolones bearing three adjacent stereogenic centers including two vicinal spiro quaternary chiral centers were obtained in high yields (up to 99% yield) with excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to 99% ee).

Original languageEnglish
Pages (from-to)5375-5380
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number21
DOIs
Publication statusPublished - 2019

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Song, Y. X., & Du, D. M. (2019). Asymmetric synthesis of spirooxindole-fused spirothiazolones via squaramide-catalysed reaction of 3-chlorooxindoles with 5-alkenyl thiazolones. Organic and Biomolecular Chemistry, 17(21), 5375-5380. https://doi.org/10.1039/c9ob00998a