ArticleAngewandte Chemie (International ed. in English)2021
Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Nickel-Catalyzed Enantioconvergent Arylation of Unactivated Cyclic Electrophiles: Asymmetric Synthesis of 3-Substituted Pyrrolidines.Angewandte Chemie (International ed. in English) · 2026Article
- Enantioselective Beckmann Rearrangement through Organocatalytic Desymmetrization of Cyclobutanones for the Synthesis of 4,4-Disubstituted γ-Lactams.Organic letters · 2026Article
- Synthesis of chiral lactams by asymmetric nitrogen insertion.Chemical science · 2026Article
- Precise control of selective nitrogen atom insertion into five-membered cyclic β-ketoesters.Nature communications · 2025Article
- Catalytic Enantioselective Synthesis of 1,4-(Hetero) Dicarbonyl Compounds through α-Carbonyl Umpolung.Journal of the American Chemical Society · 2025Article
- Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing.Acta pharmaceutica Sinica. B · 2024Review
- Monofluoromethylation ofInternational journal of molecular sciences · 2023Review
- Dynamic kinetic resolution of transient hemiketals: a strategy for the desymmetrisation of prochiral oxetanols.Chemical science · 2022Article
- Catalytic Enantioselective Synthesis of γ-Lactams with β-Quaternary Centers via Merging of C-C Activation and Sulfonyl Radical Migration.Journal of the American Chemical Society · 2022Article
- Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
5 authors.
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Abstract
Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin-Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.
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