Title: Synthesis, Chiral Separation, Barrier to Rotation and Absolute Configuration of N-(O- Functionalized-Aryl)-4-Alkyl-Thiazolin-2-One and Thiazoline-2-Thione Atropisomers
Volume: 2
Issue: 5
Author(s): N. Vanthuyne, F. Andreoli, S. Fernandez, M. Roman and C. Roussel
Affiliation:
Keywords:
heterocyclic atropisomer, barrier to rotation, absolute configuration
Abstract: The synthesis of N-(o-aryl)-4-alkyl-thiazolin-2-one atropisomers bearing hydroxy-, methoxy-, amino- or isothiocyanato- groups as ortho-substituent are described from their thiazoline-2-thione analogues. The enantiomers were obtained optically pure by semi-preparative chiral HPLC, their optical properties and absolute configurations were established. The barriers to rotation were determined and are discussed according to the nature of the substituents.