Chiral Discrimination of Organothiols via 19F NMR and a Multicomponent Reaction

This study aims to develop a sensitive and precise method for determining chiral thiols using an efficient multicomponent reaction. This innovative approach leverages the coupling of 19F-labeled chiral amines, o-phthalaldehyde, and targeted thiol analytes to rapidly generate diastereoisomeric isoindole derivatives. These derivatives exhibit distinctive 19F NMR signals, providing valuable insights for chiral discrimination. The introduction of chiral amines bearing dual 19F labels enables dual-site detection, significantly enhancing the system’s resolving capabilities. The superior resolving power of this methodology is demonstrated through the simultaneous chiral discrimination of eight chiral thiols, showcasing its potential for analyzing complex samples in biological studies and pharmaceutical development.