Regio-defined amino[5]oxa- and thiahelicenes: A dramatic impact of the nature of the heteroatom on the helical shape and racemization barriers - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2010

Regio-defined amino[5]oxa- and thiahelicenes: A dramatic impact of the nature of the heteroatom on the helical shape and racemization barriers

Résumé

The present approach to heterohelicenes provides original [5]oxa- and thiahelicenes, where both oxygen and sulfur atoms are located at the end of the inner helix. Quantum chemical calculations are carried out to determine the pathway for interconversion between two enantiomers and demonstrate that the energy barrier is strongly dependent on the nature of the heteroatompresent on the helical shape.

Domaines

Chimie organique
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Dates et versions

hal-02310992 , version 1 (10-10-2019)

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Citer

Grégory Pieters, Anne Gaucher, Sylvain R A Marque, François Maurel, Philippe Lesot, et al.. Regio-defined amino[5]oxa- and thiahelicenes: A dramatic impact of the nature of the heteroatom on the helical shape and racemization barriers. Journal of Organic Chemistry, 2010, 75 (6), pp.2096-2098. ⟨10.1021/jo1000127⟩. ⟨hal-02310992⟩
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