ArticleChem2025
Downsizing Lactams via Rh-Catalyzed C-C Activation.
Article in Chem, 2025. 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.
- Lactam Framework Editing via Formal Methylene Deletion.Journal of the American Chemical Society · 2026Article
- "Cut-and-Sew" Reactions of β-Lactams via C-C Bond Activation.Journal of the American Chemical Society · 2025Article
- Skeletal editing of 4-arylpyrimidines into diverse nitrogen heteroaromatics via four-atom synthons.Nature communications · 2025Article
- Skeletal Modification via Activation of Relatively Unstrained C-C Bonds.Accounts of chemical research · 2025Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Ring-contraction reactions are valuable transformations to access harder-to-synthesize smaller-sized rings from more available larger-sized precursors. Herein, we report an unprecedented lactam downsizing strategy by taking advantage of removable directing groups (DGs) and Rh-catalyzed C-C activation. An efficient method for DG installation to common lactam substrates is developed by employing silylated amines and Ti catalysts, and the resulting amidine moiety can be converted back to lactams via acid-mediated hydrolysis. The ring-contraction reaction exhibits a broad substrate scope, excellent functional group tolerance, and high selectivity for yielding γ-lactams, facilitating "6-to-5", "7-to-5", and "8-to-5" ring contractions. Additionally, by carefully selecting DGs and ligands, preliminary results on selective "7-to-6" ring contraction have been obtained. Finally, density functional theory (DFT) calculations reveal the origin of the product selectivity.
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Registered trials
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