ArticleChemical science2018
Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Phosphine-Catalyzed Domino Regio- and Stereo-Selective Hexamerization of 2-(Bromomethyl)acrylates to 1,2-Bis(cyclohexenyl)ethenyl Derivatives.Organic letters · 2023Article
- Enantioselective Synthesis of Quaternary Oxindoles: Desymmetrizing Staudinger-Aza-Wittig Reaction Enabled by a Bespoke HypPhos Oxide Catalyst.Journal of the American Chemical Society · 2022Article
- Review
- Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.Journal of the American Chemical Society · 2021Article
- P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.Journal of the American Chemical Society · 2020Article
- Let's Make White Phosphorus Obsolete.ACS central science · 2020Review
- An Improved PJournal of the American Chemical Society · 2020Article
- PAngewandte Chemie (International ed. in English) · 2020Article
- Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions.Molecules (Basel, Switzerland) · 2019Article
- Driving Recursive Dehydration by PJournal of the American Chemical Society · 2019Article
- Phosphine-Catalyzed α-Umpolung-Aldol Reaction for the Synthesis of Benzo[ b]azapin-3-ones.Organic letters · 2019Article
- Catalytic Asymmetric Staudinger-aza-Wittig Reaction for the Synthesis of Heterocyclic Amines.Journal of the American Chemical Society · 2019Article
- Organophosphorus-Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by PAngewandte Chemie (International ed. in English) · 2019Article
- Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PJournal of the American Chemical Society · 2018Article
- Phosphine Organocatalysis.Chemical reviews · 2018Review
- Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation.ACS catalysis · 2018Article
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Authors and funding
5 authors.
Funding
Abstract
A novel bridged [2.2.1] bicyclic phosphine oxide, devised to circumvent the waste generation and burdens of purification that are typical of reactions driven by the generation of phosphine oxides, has been prepared in three steps from commercially available cyclopent-3-ene-1-carboxylic acid. The performance of this novel phosphine oxide was superior to those of current best-in-class counterparts, as verified experimentally through kinetic analysis of its silane-mediated reduction. It has been applied successfully in halide-/base-free catalytic γ-umpolung addition-Wittig olefinations of allenoates and 2-amidobenzaldehydes to produce 1,2-dihydroquinolines with good efficiency. One of the 1,2-dihydroquinoline products was converted to known antitubercular furanoquinolines.
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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 OpenQuestion graph.