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

Abstract : 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.
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https://hal.archives-ouvertes.fr/hal-02310992
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Submitted on : Thursday, October 10, 2019 - 3:57:51 PM
Last modification on : Wednesday, October 30, 2019 - 7:07:04 AM

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Grégory Pieters, Anne Gaucher, Sylvain 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, American Chemical Society, 2010, 75 (6), pp.2096-2098. ⟨10.1021/jo1000127⟩. ⟨hal-02310992⟩

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