Synthesis, Chiral Separation, Barrier to Rotation and Absolute Configuration of N-(O- Functionalized-Aryl)-4-Alkyl-Thiazolin-2-One and Thiazoline-2-Thione Atropisomers

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.

Cite this article as:

Vanthuyne N., Andreoli F., Fernandez S., Roman M. and Roussel C., Synthesis, Chiral Separation, Barrier to Rotation and Absolute Configuration of N-(O- Functionalized-Aryl)-4-Alkyl-Thiazolin-2-One and Thiazoline-2-Thione Atropisomers, Letters in Organic Chemistry 2005; 2 (5) . https://dx.doi.org/10.2174/1570178054405931