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Journal Articles Chirality Year : 2016

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

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.

Dates and versions

hal-01928560 , version 1 (20-11-2018)

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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, 2016, 28 (2), pp.136-142. ⟨10.1002/chir.22552⟩. ⟨hal-01928560⟩
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