ArticleNature communications2024
Enantioselective synthesis of chiral amides by carbene insertion into amide N-H bond.
Article in Nature communications, 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.
- Enantioselective Pyrazole Alkylation via Iridium and Squaramide Catalyzed N-H Insertion.Journal of the American Chemical Society · 2026Article
- Cu-Catalyzed Asymmetric Carbene Insertion into N-H, O-H, and S-H Bonds: Challenging the Existing Mechanistic Dogma.JACS Au · 2025Article
- Enantioconvergent Chan-Lam Coupling: Synthesis of Chiral Benzylic Amides via Cu-Catalyzed Deborylative Amidation.Journal of the American Chemical Society · 2025Article
- DigiChemTree enables programmable light-induced carbene generation for on demand chemical synthesis.Communications chemistry · 2024Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Chiral amides are important structure in many natural products and pharmaceuticals, yet their efficient synthesis from simple amide feedstock remains challenge due to its weak Lewis basicity. Herein, we describe our study of the enantioselective synthesis of chiral amides by N-alkylation of primary amides taking advantage of an achiral rhodium and chiral squaramide co-catalyzed carbene N-H insertion reaction. This method features mild condition, rapid reaction rate (in all cases 1 min) and a wide substrate scope with high yield and excellent enantioselectivity. Further product transformations show the synthetic potential of this reaction. Mechanistic studies reveal that the non-covalent interactions between the catalyst and reaction intermediate play a critical role in enantiocontrol.
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Registered trials
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