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Enantiomerization of Allylic Trifluoromethyl Sulfoxides Studied by HPLC Analysis and DFT Calculations

Laëtitia Bailly 1 Emilie Petit 1 Mayaka Maeno 2 Norio Shibata 2 Oliver Trapp 3 Pascal Cardinaël 4 Isabelle Chataigner 1 Dominique Cahard 1 
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 Department of Frontier Materials, Department of Nanopharmaceutical Science
3 Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg,
4 SMS - Sciences et Méthodes Séparatives
Abstract : Enantiomerization of allylic trifluoromethyl sulfoxides occurs spontaneously at room temperature through the corresponding allylic trifluoromethanesulfenates via a [2,3]‐sigmatropic rearrangement. Dynamic enantioselective high‐performance liquid chromatography (HPLC) analysis revealed the stereodynamics of these sulfoxides ranging from chromatographic resolution to peak coalescence at temperatures between 5 and 53 °C. The rate constant of enantiomerization and activation parameters were determined and compared with Density Functional Theory (DFT) calculations.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01928560
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Submitted on : Tuesday, November 20, 2018 - 3:54:11 PM
Last modification on : Saturday, June 25, 2022 - 9:52:42 AM

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CNRS | INSA-ROUEN | COMUE-NORMANDIE | INC-CNRS | UNIROUEN | ENSICAEN | UNILEHAVRE | UNICAEN | COBRA | LABO-SMS | INSA-GROUPE

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Laëtitia Bailly, Emilie Petit, Mayaka Maeno, Norio Shibata, Oliver Trapp, et al.. Enantiomerization of Allylic Trifluoromethyl Sulfoxides Studied by HPLC Analysis and DFT Calculations. Chirality, Wiley, 2016, 28 (2), pp.136-142. ⟨10.1002/chir.22552⟩. ⟨hal-01928560⟩

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