Speaker
Description
Chiral sulfoxides are valuable motifs in organic synthesis, medicinal chemistry, and pharmaceutical research. The present study addresses a central methodological challenge in biochirality research: how to control, monitor, and analytically resolve stereochemical outcomes in small chiral molecules. A series of aryl sulfides bearing electron-donating and electron-withdrawing substituents at different aromatic positions was subjected to enantioselective oxidation in order to evaluate the influence of substrate electronics and substitution pattern on reactivity and stereochemical induction.1
Preliminary experiments indicate that suppression of non-selective background oxidation and optimization of the Ti:DET ratio are important for maintaining enantiomeric enrichment. Use of opposite diethyl tartrate enantiomers, R,R-DET and S,S-DET, in separate catalyst-complex formation experiments led to a reversal of enantioselectivity, with the opposite sulfoxide enantiomer becoming predominant in each case. The products are profiled by chiral HPLC on polysaccharide-based chiral stationary phases to determine enantiomeric excess and evaluate structure-selector relationships. Presented as an ongoing methodological project rather than a fully completed study, this work invites discussion on improving catalyst assembly, asymmetric oxidation conditions, and chromatographic strategies for reliable profiling of small chiral molecules relevant to biochirality research.
Keywords: HPLC, enantiomers, sulfoxides.
References: Konjaria, M.-L.; Kakava, R.; Volonterio, A.; Chankvetadze, B.; Scriba, G. K. E. Enantioseparation of chiral (benzylsulfinyl)benzamide sulfoxides by capillary electrophoresis using cyclodextrins as chiral selectors. J. Chromatogr. A 2022, 1672, 463027. https://doi.org/10.1016/j.chroma.2022.463027.