Aydin, A. Ebru2024-09-182024-09-1820130957-4166https://doi.org/10.1016/j.tetasy.2013.03.011https://hdl.handle.net/20.500.12483/13289Novel chiral norephedrine-based beta-amino alcohol ligands containing a thiophene ring were prepared from norephedrine and substituted furan carbaldehydes (methyl- or ethyl-substituted) and used in combination with VO(acac)(2) for the asymmetric oxidation of aryl methyl sulfides using H2O2 as an oxidant. Amino alcohol derived Schiff bases 4,5a-b gave higher enantiomeric excesses than amino alcohol-derived reduced Schiff based ligands 6,7a-b. Of these chiral ligands, (1S,2R)-5b and (1S,2R)-7b gave high yields (90%) with moderate to high enantioselectivities (78%, 96% ee, respectively). The oxidation of other aryl methyl sulfides with (1S,2R)-5b and (1S,2R)-7b as ligands afforded the corresponding sulfoxides in 60-89% yields and with 92-99% ee. (C) 2013 Elsevier Ltd. All rights reserved.eninfo:eu-repo/semantics/closedAccessHighly Enantioselective OxidationHydrogen-PeroxideKinetic ResolutionSchiff-BasesVanadium CatalystsTitanium ComplexesProchiral SulfidesMetal-ComplexesAryl SulfidesDerivativesArticle24844444810.1016/j.tetasy.2013.03.0112-s2.0-84876383293N/AWOS:000318326300004Q2