ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2024
Bifunctional Squaramide-Catalyzed Oxidative Kinetic Resolution: Simultaneous Access to Axially Chiral Thioether and Sulfoxide.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Stereogenic S‑Induced Generation of Axially Chiral Cyclic Vinyl Sulfinamides and Serendipitous Diastereomeric Enrichment.JACS Au · 2026Article
- Recent Advances in Organocatalytic Kinetic Resolution for the Synthesis of Axially Chiral Compounds.Molecules (Basel, Switzerland) · 2026Review
- Imidazolium-based ionic liquid functionalized chiral metal-organic framework as an efficient catalyst for asymmetric catalytic sulfoxidation.RSC advances · 2025Article
- Bifunctional Squaramide-Catalyzed Oxidative Kinetic Resolution: Simultaneous Access to Axially Chiral Thioether and Sulfoxide.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
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Authors and funding
5 authors.
Funding
Abstract
Axially chiral thioethers and sulfoxides emerge as two pivotal classes of ligands and organocatalysts, which have remarkable features in the stereoinduction of various asymmetric transformations. However, the lack of easy methods to access such molecules with diverse structures has hampered their broader utilization. Herein, an oxidative kinetic resolution for sulfides using a chiral bifunctional squaramide as the catalyst with cumene hydroperoxide as the terminal oxidant is established. This asymmetric approach provides a variety of axially chiral thioethers as well as sulfoxides bearing both axial and central chirality, with excellent diastereo- and enantioselectivities. This catalytic system also successfully extends to the kinetic resolution of benzothiophene-based sulfides. Preliminary mechanism investigation indicates that the multiple hydrogen bonding interactions between the bifunctional squaramide catalyst and substrates play a crucial role in determining the enantioselectivity and reactivity.
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