Title of article :
Synthesis, Chiral Separation, Barrier To Rotation And Absolute Configuration Of N-(O-Functionalized-Aryl)-4-Alkyl-Thiazolin-2-One And Thiazoline-2-Thione Atropisomers
Author/Authors :
Vanthuyne, Nicolas Université Paul Cézanne – Aix-Marseille III - Laboratoire de Stéréochimie Dynamique et Chiralité, France , Andreoli, Federico Université Paul Cézanne – Aix-Marseille III - Laboratoire de Stéréochimie Dynamique et Chiralité, France , Fernandez, Sylvie Université Paul Cézanne – Aix-Marseille III - Laboratoire de Stéréochimie Dynamique et Chiralité, France , Roman, Mihaela Université Paul Cézanne – Aix-Marseille III - Laboratoire de Stéréochimie Dynamique et Chiralité, France , Roussel, Christian Université Paul Cézanne – Aix-Marseille III - Laboratoire de Stéréochimie Dynamique et Chiralité, France
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.
Keywords :
Heterocyclic atropisomer , barrier to rotation , absolute configuration
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
