Diastereoselective reversible C–C bond exchange of oxindole–thiazolidienediones for dynamic combinatorial chemistry. Issue 47 (18th November 2022)

• Record Type: Journal Article
• Authors: Gorai, Ananta; Chakraborti, Gargi; Basak, Soumya Jyoti; Dash, Jyotirmayee
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 47(2022)
• Page Start: 9307
• Page End: 9312
• Publication Date: 2022-11-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01993k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A metal and organic catalyst free diastereoselective aldol exchange under physiological conditions, suitable for the generation of dynamic combinatorial libraries (DCLs) has been described. Abstract : We herein describe a diastereoselective aldol exchange involving isatins and thiazolidinediones, providing oxindolyl-thiazolidienediones in aqueous media at pH 6. This equilibrium can also be achieved with oxindole exchange as well as cross-exchange within reasonable timescales. These metal and organic catalyst free reversible reactions provide a unique opportunity for the evolution of dynamic combinatorial libraries (DCLs) for target directed dynamic combinatorial chemistry (DCC) and system chemistry.