Asymmetric synthesis of modafinil and its derivatives by enantioselective oxidation of thioethers: comparison of various methods including synthesis in ionic liquids

The oxidation of 2-(benzhydrylthio)acetic acid and its derivatives was performed with various catalytic and stoichiometric enantioselective reagents, the best results being obtained with stoichiometric chiral oxaziridine 5. The use of [bmim][PF 6] as a solvent with 5 gave slightly higher yields and,...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 18; no. 24; pp. 2959 - 2964
Main Authors Ternois, James, Guillen, Frédéric, Plaquevent, Jean-Christophe, Coquerel, Gérard
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.12.2007
Elsevier
Subjects
Chemical Sciences
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Organic chemistry
Physical Sciences
Science & Technology
REAGENT
SULFOXIDES
OXAZIRIDINES
ELECTROPHILIC FLUORINATION
SOLVENTS
SULFIDE OXIDATION
CHEMISTRY
H2O2
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Summary:The oxidation of 2-(benzhydrylthio)acetic acid and its derivatives was performed with various catalytic and stoichiometric enantioselective reagents, the best results being obtained with stoichiometric chiral oxaziridine 5. The use of [bmim][PF 6] as a solvent with 5 gave slightly higher yields and, in the case of the model compound thioanisole, a reversal of the enantioselectivity.
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/j.tetasy.2007.11.031