A squaramide-catalysed asymmetric cascade Michael addition/acyl transfer reaction between unsaturated benzothiophenones and α-nitroketones

Cheng Niu, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

An efficient and practical organocatalytic asymmetric strategy was developed using unsaturated benzothiophenones and α-nitroketones catalysed by bifunctional squaramide via Michael addition and acyl transfer steps. A broad range of chiral acyloxybenzothiophene derivatives were obtained in good yields (up to 97%) with excellent enantioselectivities (up to 98% ee). What's more, employing different chiral squaramide catalysts and unsaturated benzothiophenones can deliver the acyloxy unit at the 2-position or 3-position of benzothiophene.

Original languageEnglish
Pages (from-to)840-846
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume20
Issue number4
DOIs
Publication statusPublished - 28 Jan 2022

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Niu, C., & Du, D. M. (2022). A squaramide-catalysed asymmetric cascade Michael addition/acyl transfer reaction between unsaturated benzothiophenones and α-nitroketones. Organic and Biomolecular Chemistry, 20(4), 840-846. https://doi.org/10.1039/d1ob02217b