ArticleJournal of the American Chemical Society2024
Chemoselective Diazine Dearomatization: The Catalytic Enantioselective Dearomatization of Pyrazine.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
3 citing papers in PubMed, 13 citations in OpenAlex.
- Efficient Approaches to the Design of Six-Membered Polyazocyclic Compounds-Part 2: Nonaromatic Frameworks.Molecules (Basel, Switzerland) · 2025Review
- Asymmetric Rh-Catalyzed Synthesis of Dihydronicotinamides.The Journal of organic chemistry · 2025Article
- Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes.Journal of the American Chemical Society · 2024Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Despite much progress in the area of dearomatization, the enantioselective dearomatization of heterocycles is limited to those with a single heteroatom. Here we report a highly enantioselective copper-catalyzed dearomatization of pyrazine, a diazine, leading to chiral C-substituted piperazines. When exposed to a chloroformate and an alkyne in the presence of a catalyst derived from a copper salt and the chiral ligand StackPhos, pyrazine is readily dearomatized to provide a 2,3-disubstituted dihydropyrazine as single diastereomer in high enantiomeric excess. Mechanistic studies support a noninnocent involvement of chloride ion preventing a second iminium alkynylation, thus enabling subsequent functionalization at the second reactive site. The synthetically useful dihydropyrazine products, obtained in up to 95% yield and 99% ee, can be further manipulated to form optically active C-substituted piperazines and
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Registered trials
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