The synthesis and application of pyrrolidine-based supported catalysts

Abstract

Abstract A helical polymer (poly- 2 200 ) is synthesized which contains a pyrrolidine structure using ( S )-(aminomethyl)-1-boc-pyrrolidine as the starting material. The catalyst demonstrates significant solvent-dependent stereoselectivity in asymmetric aldol reactions, with chloroform emerging as the optimal medium achieving enantiomeric excess ( ee ) of 68.4 % and a diastereomeric ratio ( dr ) of 73:27 for the cyclohexanone-4-nitrobenzaldehyde coupling. The catalyst exhibits broad substrate compatibility, processing electron-deficient aromatic aldehydes (4-CN, 4-NO 2 , 2-CF 3 ) with distinct stereochemical outcomes. Particularly noteworthy is the catalyst’s ability to maintain moderate enantiocontrol (46.8 % ee ) even with sterically demanding 2-(trifluoromethyl)benzaldehyde. This indicates that the catalyst has relatively good catalytic activity and shows excellent application prospects in asymmetric catalysis.