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

Authors: Vanthuyne, N.; Andreoli, F.; Fernandez, S.; Roman, M.; Roussel, C.

Source: Letters in Organic Chemistry, Volume 2, Number 5, August 2005 , pp. 433-443(11)

Publisher: Bentham Science Publishers

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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: absolute configuration; barrier to rotation; heterocyclic atropisomer

Document Type: Review Article

DOI: http://dx.doi.org/10.2174/1570178054405931

Affiliations: UMR “Chirotechnologies: Catalyse et Biocatalyse”, Universite Paul Cezanne, Avenue Escadrille Normandie-Niemen, Case A62, 13397 Marseille cedex 20, France.

Publication date: August 1, 2005

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
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