Chromatographic Enantioseparation of Chiral Sulfoximines on Polysaccharide-Based Chiral Stationary Phases.

J Chromatogr Sci

College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, #1 East Third Road, Erxianqiao, Chenghua District, Chengdu 610059, China.

Published: November 2023

Chiral sulfoximines have significant roles in pharmaceutical industry and agricultural chemicals. Furthermore, chiral structurally related sulfoximines are used for their wide potential applications in some uncharted territory. However, chromatographic study on these compounds has not been systematically performed. Herein, this paper describes the enantioseparation of 12 chiral sulfoximines on polysaccharide-based chiral stationary phases (CSPs). Separation factors of chiral column, high-performance liquid chromatography parameters such as mobile phase composition and column temperature were carefully investigated. Chiralcel OJ-H column can resolve all of the 12 compounds, while Chiralpak AD-H column and Chiralpak AS-H column can separate eight and nine molecules, respectively. The sulfoximines are effectively resolved with Chiralcel OJ-H column with a mixture of n-hexane/2-propanol (80:20) as the mobile phase.

Download full-text PDF

Source
http://dx.doi.org/10.1093/chromsci/bmad046DOI Listing

Publication Analysis

Top Keywords

chiral sulfoximines
12
enantioseparation chiral
8
sulfoximines polysaccharide-based
8
polysaccharide-based chiral
8
chiral stationary
8
stationary phases
8
mobile phase
8
chiralcel oj-h
8
oj-h column
8
chiral
7

Similar Publications

Synthesis and Functionalization of Sulfoximine-Bicyclo[1.1.0]butanes: Functionalizable, Tuneable and Cysteine-Selective Chiral Warheads.

Angew Chem Int Ed Engl

November 2024

Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London, W12 0BZ, UK.

Electrophilic covalent warheads with appropriate reactivity and selectivity are crucial to the investigation of protein function and the discovery of therapeutics. Here we report the synthesis of sulfoximine bicyclo[1.1.

View Article and Find Full Text PDF

Photoinduced Asymmetric Alkene Aminohetarylation with Chiral Sulfoximine Reagents.

Angew Chem Int Ed Engl

November 2024

Frontiers Science Center for Transformative Molecules, Zhangjiang Institute for Advanced Study and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.

Given the pivotal role of β-(het)arylethylamine moiety in bioactive molecules, the direct amino(het)arylation of alkenes occupies a privileged position in the construction of (het)arylethylamine derivatives. Herein we devise chiral sulfoximines as novel bifunctional reagents which exhibit remarkable efficiency in the challenging asymmetric alkene aminohetarylation reaction, particularly in terms of reactivity and stereo-control. The chiral reagents can be conveniently accessed in gram scale, and efficiently generate N-centered radicals under mild photochemical conditions.

View Article and Find Full Text PDF

Efforts aimed at enriching the chemical and structural diversity of small molecules have invigorated synthetic exploration in the last two decades. Spatially defined molecular functionality serves as the foundation to construct unique chemical space to further advance discovery science. The chiral SuFEx reagent t-BuSF provides a modular platform for the stereocontrolled bifunctionalization of sulfur.

View Article and Find Full Text PDF

Enantioselective S-Alkylation of Sulfenamides by Phase-Transfer Catalysis.

Angew Chem Int Ed Engl

October 2024

Department of Chemistry, Yale University, 225 Prospect St., New Haven, CT 06520, USA.

A general phase-transfer catalyst (PTC) mediated enantioselective alkylation of N-acylsulfenamides is reported. Essential to achieving high selectivity was the use of the triethylacetyl sulfenamide protecting group along with aqueous KOH as the base under biphasic aqueous conditions to enable the reaction to be performed at -40 °C. With these key parameters, enantiomeric ratios up to 97.

View Article and Find Full Text PDF

Enantioselective Arylation of Sulfenamides to Access Sulfilimines Enabled by Palladium Catalysis.

Angew Chem Int Ed Engl

September 2024

Department of Chemistry, Fudan University, 2205 Songhu Road, Shanghai, 200438, China.

Sulfur-containing functional groups have garnered considerable attention due to their common occurrence in ligands, pharmaceuticals, and insecticides. Nevertheless, enantioselective synthesis of sulfilimines, particularly diaryl sulfilimines remains a challenging and persistent goal. Herein we report a highly enantio- and chemoselective cross-coupling of sulfenamides with aryl diazonium salt to construct diverse S(IV) stereocenters by Pd catalysis.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!