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(s): N. Vanthuyne, F. Andreoli, S. Fernandez, M. Roman, C. Roussel

Journal Name: Letters in Organic Chemistry

Volume 2 , Issue 5 , 2005

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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

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Article Details

Year: 2005
Page: [433 - 443]
Pages: 11
DOI: 10.2174/1570178054405931
Price: $65

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PDF: 11