Asymmetric synthesis of spirocyclic isobenzofuranones via a squaramide-catalysed sulfa-Michael desymmetrisation reaction. Issue 12 (7th March 2023)

• Record Type: Journal Article
• Authors: Tamanna, ; Sharma, Deepak; Chauhan, Pankaj
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 12(2023)
• Page Start: 2570
• Page End: 2574
• Publication Date: 2023-03-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d3ob00126a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Herein, we describe the enantioselective synthesis of spirocyclohexenone isobenzofuranones through a sulfa-Michael addition/desymmetrization reaction catalyzed by a squaramide organocatalyst. Abstract : Enantioselective synthesis of spirocyclohexenone isobenzofuranones has been achieved through an organocatalysed sulfa-Michael desymmetrisation reaction. A cinchona-derived squaramide effectively promotes the desymmetrisation of spirocyclic 2, 5-cyclohexadienone isobenzofuranones via the controlled addition of various aryl thiols to generate two vicinal stereocenters with perfect diastereoselectivities and up to very good enantioselectivities.