ArticleChemical science2022
Divergent stereochemical outcomes in the insertion of donor/donor carbenes into the C-H bonds of stereogenic centers.
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 16 citations in OpenAlex.
- Remote Stereocontrol in Aryl/Alkyl C-H Insertion Reactions of Rhodium Carbenes: Assembly of Pseudorigidols A and B.Organic letters · 2026Article
- Characterization of a Silver Vinylcarbene Intermediate in Carbene-Alkyne Metathesis and Its Concerted C(spJournal of the American Chemical Society · 2026Article
- Enantioselective Synthesis of Complex Carbocycles by C-H Insertion of Aryl/Aryl Carbenes.ACS catalysis · 2025Article
- Asymmetric Synthesis of Cycloartobiloxanthone.Organic letters · 2025Article
- Ligand-controlled divergent asymmetric C(spNature communications · 2025Article
- Assembly of the Tricyclic Core of Alopecurone C by Asymmetric Donor/Donor Carbene C-H Insertion.Organic letters · 2024Article
- Deconvoluting Nonlinear Catalyst-Substrate Effects in the Intramolecular Dirhodium-Catalyzed C-H Insertion of Donor/Donor Carbenes Using Data Science Tools.ACS catalysis · 2024Article
- Intramolecular Interception of the Remote Position of Vinylcarbene Silver Complex Intermediates by C(spAngewandte Chemie (International ed. in English) · 2023Article
- Palladium-catalyzed intramolecular enantioselective C(spChemical science · 2022Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Intramolecular C-H insertions with donor/donor dirhodium carbenes provide a concise and highly stereoselective method to set two contiguous stereocenters in a single step. Herein, we report the insertion of donor/donor carbenes into stereogenic carbon centers allowing access to trisubstituted benzodihydrofurans in a single step. This study illuminates, for the first time, the stereochemical impact on the carbene center and delineates the structural factors that enable control over both stereogenic centers. Sterically bulky, highly activated C-H insertion centers exhibit high substrate control yielding a single diastereomer and a single enantiomer of product regardless of the catalyst used. Less bulky, less activated C-H insertion centers exhibit catalyst control over the diastereomeric ratio (dr), where a single enantiomer of each diastereomer is observed with high selectivity. A combination of experimental studies and DFT calculations was used to elucidate the origin of these results. First, hydride transfer from the stereogenic insertion site proceeds with high stereoselectivity to the carbene center, thus determining the absolute configuration of the product. Second, the short lived zwitterionic intermediate can diaster-eoselectively ring-close by a hitherto unreported S
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