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

Bailly Laetitia | Zendy; Petit Emilie | Zendy; Maeno Mayaka | Zendy; Shibata Norio | Zendy; Trapp Oliver | Zendy; Cardinael Pascal | Zendy; Chataigner Isabelle | Zendy; Cahard Dominique | Zendy

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

Author(s) -

Bailly Laetitia,

Petit Emilie,

Maeno Mayaka,

Shibata Norio,

Trapp Oliver,

Cardinael Pascal,

Chataigner Isabelle,

Cahard Dominique

Publication year - 2016

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.22552

Subject(s) - chemistry , allylic rearrangement , trifluoromethyl , high performance liquid chromatography , coalescence (physics) , enantioselective synthesis , density functional theory , chromatography , medicinal chemistry , computational chemistry , organic chemistry , catalysis , alkyl , physics , astrobiology

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. Chirality 28:136–142, 2016 . © 2015 Wiley Periodicals, Inc.

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