A squaramide-catalysed asymmetric cascade Michael addition/acyl transfer reaction between unsaturated benzothiophenones and α-nitroketones. Issue 4 (12th January 2022)

• Record Type: Journal Article
• Authors: Niu, Cheng; Du, Da-Ming
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 4(2022)
• Page Start: 840
• Page End: 846
• Publication Date: 2022-01-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02217b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A practical organocatalytic asymmetric synthesis of chiral acyloxybenzothiophene derivatives was developed using unsaturated benzothiophenones and α-nitroketones catalysed by squaramide via Michael addition/acyl transfer cascade reactions. 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.