ArticleAngewandte Chemie (International ed. in English)2025
Shaping of a Reactive Manganese Catalyst Enables Access to Polyfunctionalized Cyclohexanes via Enantioselective C(sp
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Iron-Catalyzed Asymmetric NHAngewandte Chemie (International ed. in English) · 2026Article
- Heteronuclear Neighboring Co-Mn Single-Atom Pairs as a Synergistic Platform for Oxidative C-H Functionalization.Angewandte Chemie (International ed. in English) · 2026Article
- Installing Axial Chirality by Atroposelective C(spJournal of the American Chemical Society · 2026Article
- Desymmetrization of Malonic Monoesters and Malonic Acids via Enantioselective Catalytic C(spAngewandte Chemie (International ed. in English) · 2026Article
- Bimolecular Homolytic Substitution (SACS central science · 2025Review
- Shaping of a Reactive Manganese Catalyst Enables Access to Polyfunctionalized Cyclohexanes via Enantioselective C(spAngewandte Chemie (International ed. in English) · 2025Article
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8 authors.
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Abstract
Chiral polyoxygenated cyclohexanes are valuable constituents of biologically relevant products. Herein, we report a protocol for the direct access to these scaffolds via site- and enantioselective non-directed oxidation of cyclohexyl-3,5-meso diethers using aqueous H₂O₂. Structural shaping of a highly reactive chiral Mn-oxo species, achieved through the combination of a sterically encumbered ligand and a bulky carboxylic acid, promotes a precise fit of the substrate within the catalyst pocket, which translates into exceptional enantioselectivity (up to >99% ee). Computational studies reveal that C─H oxidation proceeds via an initial hydrogen atom transfer, followed by electron transfer, leading to the formation of a chiral cationic intermediate. The resulting desymmetrized 3-methoxycyclohexanone products serve as valuable intermediates for the synthesis of bioactive cores, as they can undergo orthogonal chemical modifications to enable further structural diversification.
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