ArticleChemical science2020
What is the role of acid-acid interactions in asymmetric phosphoric acid organocatalysis? A detailed mechanistic study using interlocked and non-interlocked catalysts.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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19 citing papers in PubMed, 52 citations in OpenAlex.
- Role of 2-Hydroxyimines in Chiral Phosphoric Acid-Catalyzed Mannich-Type Reactions: Enhancing Reactivity and Selectivity via Dimerization.Journal of the American Chemical Society · 2026Article
- Catalytic Enantioselective Elimination of Cyclobutanols.Journal of the American Chemical Society · 2026Article
- Catalytic Enantioselective Synthesis of 1,1-Disubstituted Isochromans.Journal of the American Chemical Society · 2026Article
- The impact of supramolecular self-association of organocatalysts on catalytic performance.Nature reviews. Chemistry · 2025Review
- Hydrogen-Bond-Assisted Chalcogen Transfer between Phosphine Selenides and Arsine Oxides.Inorganic chemistry · 2025Article
- The Elusive Ternary Intermediates of Chiral Phosphoric Acids in Ion Pair Catalysis─Structures, Conformations, and Aggregation.Journal of the American Chemical Society · 2025Article
- 3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units.Beilstein journal of organic chemistry · 2025Article
- Helical polyisocyanide-based macroporous organic catalysts for asymmetric Michael addition with high efficiency and stereoselectivity.Chemical science · 2024Article
- Highly acidicChemical science · 2024Article
- Dimerization of confined Brønsted acids in enantioselective organocatalytic reactions.Chemical science · 2023Article
- A Brief Introduction to Chemical Reaction Optimization.Chemical reviews · 2023Review
- Multifunctional Organocatalysts - Singly-Linked and Macrocyclic Bisphosphoric Acids for Asymmetric Phase-Transfer and Brønsted-Acid Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Bidentate substrate binding in Brønsted acid catalysis: structural space, hydrogen bonding and dimerization.Chemical science · 2022Article
- Distinctive features and challenges in catenane chemistry.Chemical science · 2022Review
- Controlling catalyst activity, chemoselectivity and stereoselectivity with the mechanical bond.Nature reviews. Chemistry · 2022Review
- BINOL as a chiral element in mechanically interlocked molecules.Beilstein journal of organic chemistry · 2022Review
- Association Equilibria of Organo-Phosphoric Acids with Imines from a Combined Dielectric and Nuclear Magnetic Resonance Spectroscopy Approach.Analytical chemistry · 2021Article
- Functional Rotaxanes in Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Mechanism and origins of selectivity in the enantioselective oxa-Pictet-Spengler reaction: a cooperative catalytic complex from a hydrogen bond donor and chiral phosphoric acid.Chemical science · 2020Article
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Authors and funding
9 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Organocatalysis has revolutionized asymmetric synthesis. However, the supramolecular interactions of organocatalysts in solution are often neglected, although the formation of catalyst aggregates can have a strong impact on the catalytic reaction. For phosphoric acid based organocatalysts, we have now established that catalyst-catalyst interactions can be suppressed by using macrocyclic catalysts, which react predominantly in a monomeric fashion, while they can be favored by integration into a bifunctional catenane, which reacts mainly as phosphoric acid dimers. For acyclic phosphoric acids, we found a strongly concentration dependent behavior, involving both monomeric and dimeric catalytic pathways. Based on a detailed experimental analysis, DFT-calculations and direct NMR-based observation of the catalyst aggregates, we could demonstrate that intermolecular acid-acid interactions have a drastic influence on the reaction rate and stereoselectivity of asymmetric transfer-hydrogenation catalyzed by chiral phosphoric acids.
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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.