ArticleJournal of the American Chemical Society2015
Use of a new spirophosphine to achieve catalytic enantioselective [4 + 1] annulations of amines with allenes to generate dihydropyrroles.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
What it found
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Who cites it
22 citing papers in PubMed, 137 citations in OpenAlex.
- Transition from Kwon [4+2]- to [3+2]-cycloaddition enabled by AgF-assisted phosphine catalysis.Nature communications · 2024Article
- Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles.Chemical science · 2024Article
- Asymmetric Photoaerobic Lactonization and Aza-Wacker Cyclization of Alkenes Enabled by Ternary Selenium-Sulfur Multicatalysis.ACS catalysis · 2023Article
- Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review.Molecules (Basel, Switzerland) · 2023Review
- Phosphine-catalyzed activation of cyclopropenones: a versatile CChemical science · 2022Article
- Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes.Chemical science · 2022Article
- Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates.ChemCatChem · 2020Article
- Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.Organic letters · 2019Article
- Organophosphine-Catalyzed [4C+X] Annulations.Molecules (Basel, Switzerland) · 2018Review
- Phosphine Organocatalysis.Chemical reviews · 2018Review
- Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates.Asian journal of organic chemistry · 2018Article
- An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhChemical science · 2018Article
- Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones withChemical science · 2018Article
- Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides.Organic letters · 2018Article
- Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranonesChemical science · 2017Article
- Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid.Chemical science · 2017Article
- Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines.Angewandte Chemie (International ed. in English) · 2017Article
- Asymmetric cyanation of imines via dipeptide-derived organophosphine dual-reagent catalysis.Nature communications · 2016Article
- Asymmetric copper-catalyzed C-N cross-couplings induced by visible light.Science (New York, N.Y.) · 2016Article
- Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.Aldrichimica acta · 2016Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Due in part to the common occurrence of five-membered nitrogen heterocycles in bioactive molecules, the discovery of methods for the enantioselective synthesis of such structures is a useful endeavor. Building on a single example by Tong of a phosphine-catalyzed [4 + 1] annulation of an amine with an allene that furnished an achiral dihydropyrrole in 22% yield, we have developed, with the aid of a new chiral spirophosphine catalyst, a method with increased utility, specifically, improved yield, enhanced scope (the use of γ-substituted allenes), and good ee. The enantioenriched dihydropyrrole products can be transformed into other interesting families of compounds with very good stereoselectivity.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the Socratic graph.