Chiral C2‐symmetric bis‐thioureas as enzyme mimics in enantioselective Michael addition. Issue 6 (18th March 2022)

• Record Type: Journal Article
• Authors: Cruz, Harold; Servín, Felipe A.; Aguirre, Gerardo; Pérez, Sergio; Madrigal, Domingo; Chávez, Daniel; Cooksy, Andrew L.; Somanathan, Ratnasamy
• Is Part Of: Chirality. Volume 34:Issue 6(2022)
• Page Start: 877
• Page End: 886
• Publication Date: 2022-03-18
• Subjects: 3‐bis‐thiourea -- C2‐symmetric 1 -- enantioselective Michael addition -- heterogeneous -- homogeneous -- mimicking enzyme -- organocatalysts -- supramolecular hydrogen bonding; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.23438
• Languages: English
• ISSNs: 0899-0042

Abstract

Abstract: We report herein the synthesis and application of enantiopure C2 ‐symmetric primary amine‐1, 3‐bis‐thiourea organocatalysts in enantioselective conjugate 1, 4‐Michael addition of carbonyl containing nucleophiles, to nitroalkenes and N ‐phenylmaleimide, leading to final products in good enantioselectivities (up to 99%) and yields (up to 99%). We propose supramolecular noncovalent interactions within the organocatalyst's cleft between the substrate and the catalyst, via hydrogen bonding. Supramolecular interaction thus lowers the transition state energy mimicking an enzyme. Mechanism underlying our experimental results is supported by theorical calculations. Abstract :