Engineered Immobilised Organocatalysts for the Synthesis of Chiral Amines

• Published in: Advanced synthesis & catalysis Vol. 366; no. 4; pp. 892 - 899
• Main Authors: Maciá, María, Muñoz, Iván, Porcar, Raúl, Cirujano, Francisco G., Altava, Belen, Luis, Santiago V., García‐Verdugo, Eduardo
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 20.02.2024; Wiley Subscription Services, Inc
• Subjects: Amides; Amines; asymmetric catalysis; Asymmetry; Carbonyls; Catalysts; Chemistry; Chemistry, Applied; Chemistry, Organic; continuous flow; Design factors; imine reduction; Imines; immobilized catalyst; organocatalysis; Physical Sciences; Science & Technology; Stability criteria; organocatalysis; continuous flow; IMINES; imine reduction; ASYMMETRIC REDUCTION; immobilized catalyst; asymmetric catalysis; TRICHLOROSILANE
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.202301221

The art of tuning functional polymeric materials through the covalent incorporation of organocatalysts lies at the core of creating asymmetric immobilized chiral catalysts that mimic the enzymatic action. Herein, we explore diverse synthetic techniques to immobilize l‐proline‐derived N‐carbonyl amides on functional polymeric matrices, transforming them into chiral Lewis bases for facilitating the asymmetric reduction of ketimines with HSiCl3. A comprehensive examination of the design factors, encompassing linker selection, anions, and polymeric support characteristics, enables precise adjustment of steric and electronic features in these immobilized catalysts. This approach establishes structure‐performance relationships, ultimately enabling the development of an engineered immobilized organocatalytic system that meets the desired criteria for activity, stability, and selectivity.