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

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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).

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

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Publication details

The article was received on 01 May 2019, accepted on 14 May 2019 and first published on 15 May 2019


Article type: Paper
DOI: 10.1039/C9OB00998A
Org. Biomol. Chem., 2019, Advance Article

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

    Y. Song and D. Du, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00998A

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