ArticleJournal of the American Chemical Society2022
Excited-State Copper-Catalyzed [4 + 1] Annulation Reaction Enables Modular Synthesis of α,β-Unsaturated-γ-Lactams.
Article in Journal of the American Chemical Society, 2022. 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.
- Diastereospecific Synthesis of Vicinally Substituted 2-Oxazolidinones via Oxidative Rearrangement of α,β-Unsaturated γ-Lactams.The Journal of organic chemistry · 2025Article
- Visible Light-Driven Excited-State Copper-BINAP Catalysis for Accessing Diverse Chemical Reactions.Chem catalysis · 2024Article
- Harnessing Bromo/Acyloxy Transposition (BrAcT) and Excited-State Copper Catalysis for Styrene Difunctionalization.Journal of the American Chemical Society · 2024Article
- Article
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7 authors.
Funding
Abstract
Synthesis of α,β-unsaturated-γ-lactams continue to attract attention due to the importance of this structural motif in organic chemistry. Herein, we report the development of a visible-light-induced excited-state copper-catalyzed [4 + 1] annulation reaction for the preparation of a wide range of γ-H, -OH, and -OR-substituted α,β-unsaturated-γ-lactams using acrylamides as the 4-atom unit and aroyl chlorides as the 1-atom unit. This modular synthetic protocol features mild reaction conditions, broad substrate scope, and high functional group tolerance. The reaction is amenable to late-stage diversification of complex molecular architectures, including derivatives of marketed drugs. The products of the reaction can serve as versatile building blocks for further derivatization. Preliminary mechanistic studies suggest an inner-sphere catalytic cycle involving photoexcitation of the Cu(BINAP) catalyst, single-electron transfer, and capture of radical intermediates by copper species, followed by reductive elimination or protonation to give the desired γ-functionalized α,β-unsaturated-γ-lactams.
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