ArticleJournal of the American Chemical Society2011
Transition-state charge stabilization through multiple non-covalent interactions in the guanidinium-catalyzed enantioselective Claisen rearrangement.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed.
- Article
- Selective Noncovalent Catalysis with Small Molecules.Chemical reviews · 2025Review
- Catalysis of an SNature · 2024Article
- Article
- Molecular Understanding and Practical In Silico Catalyst Design in Computational Organocatalysis and Phase Transfer Catalysis-Challenges and Opportunities.Molecules (Basel, Switzerland) · 2023Review
- Exploring Structure-Function Relationships of Aryl Pyrrolidine-Based Hydrogen-Bond Donors in Asymmetric Catalysis Using Data-Driven Techniques.ACS catalysis · 2022Article
- On the Role of Noncovalent Ligand-Substrate Interactions in Au(I) Catalysis: An Experimental and Computational Study of Protodeauration.ACS catalysis · 2022Article
- How Robust Is the Reversible Steric Shielding Strategy for Photoswitchable Organocatalysts?The Journal of organic chemistry · 2022Article
- Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.Angewandte Chemie (International ed. in English) · 2021Article
- Organocatalyst-controlled site-selective arene C-H functionalization.Nature chemistry · 2021Article
- A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.Journal of the American Chemical Society · 2021Article
- Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions.Journal of the American Chemical Society · 2021Article
- Enantioselective Catalysis of an Anionic Oxy-Cope Rearrangement Enabled by Synergistic Ion Binding.Israel journal of chemistry · 2020Article
- Why do thioureas and squaramides slow down the Ireland-Claisen rearrangement?Beilstein journal of organic chemistry · 2019Article
- Review
- The Cation-π Interaction in Small-Molecule Catalysis.Angewandte Chemie (International ed. in English) · 2016Review
- Accessing and predicting the kinetic profiles of homogeneous catalysts from volcano plots.Chemical science · 2016Article
- Catalytic, asymmetric difluorination of alkenes to generate difluoromethylated stereocenters.Science (New York, N.Y.) · 2016Article
- Synergistic Ion-Binding Catalysis Demonstrated via an Enantioselective, Catalytic [2,3]-Wittig Rearrangement.ACS central science · 2016Article
- Practical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biaryls.Angewandte Chemie (International ed. in English) · 2016Article
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Abstract
The mechanism by which chiral arylpyrrole-substituted guanidinium ions promote the Claisen rearrangement of O-allyl α-ketoesters and induce enantioselectivity was investigated by experimental and computational methods. In addition to stabilization of the developing negative charge on the oxallyl fragment of the rearrangement transition state by hydrogen-bond donation, evidence was obtained for a secondary attractive interaction between the π-system of a catalyst aromatic substituent and the cationic allyl fragment. Across a series of substituted arylpyrrole derivatives, enantioselectivity was observed to vary predictably according to this proposal. This mechanistic analysis led to the development of a new p-dimethylaminophenyl-substituted catalyst, which afforded improvements in enantioselectivity relative to the parent phenyl catalyst for a representative set of substrates.
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