ArticleChemical science2015
Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts.
Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- De-epimerizing DyKAT of β-lactones generated by isothiourea-catalysed enantioselective [2 + 2] cycloaddition.Chemical science · 2024Article
- Catalytic enantioselective synthesis of 1,4-dihydropyridinesChemical science · 2021Article
- Generation and Reactivity of C(1)-Ammonium Enolates by Using Isothiourea Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines.Molecules (Basel, Switzerland) · 2017Review
- Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Review
- [3 + 2]-Cycloadditions of Azomethine Imines and Ynolates.Organic letters · 2016Article
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Authors and funding
4 authors.
Funding
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Abstract
The addition of an organic catalyst to the ketone moiety of a γ-mono-chloride substituted cyclobutenone destroys its stable, conjugated and nearly planar structure. The C-C bond in the resulting less stable anionic oxy-substituted non-planar intermediate is then activated. The breaking of one C-C single bond leads to a catalyst-bound intermediate that undergoes α-carbon selective reactions with azomethine imines to afford nitrogen-containing heterocyclic compounds with excellent diastereo- and enantio-selectivities. Our organocatalytic approach provides a new reaction pattern for C-C bond activation of cyclobutenones that is unavailable with transition metal catalysis. In addition, the present study with isothioureas as the organocatalysts expands the potential in using organocatalysts for C-C bond breaking and selective reactions.
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Registered trials
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