ArticleScience (New York, N.Y.)2017
Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis.
Article in Science (New York, N.Y.), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 53 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
53 citing papers in PubMed, 205 citations in OpenAlex.
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- Size and Polarizability as Design Principles for Stereoselective Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- An anion-binding approach to enantioselective photoredox catalysis.Science (New York, N.Y.) · 2025Article
- Chiral Hydrogen-Bond Donor and Gold(I) Cocatalysis Enables Enantioselective Dearomative Spirocyclization of Naphthols.Journal of the American Chemical Society · 2025Article
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- Catalytic Enantioselective Perezone-Type [5 + 2] Cycloaddition.Journal of the American Chemical Society · 2025Article
- Hydrogen Bond Promoted Carbonylative Lactonization of Alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Gold-catalyzed highly enantioselective cycloadditions of 1,6-enynes and 1,6-diynes assisted by remote hydrogen bonding interaction.iScience · 2024Article
- A Ligand-Controlled Approach Enabling Gold(I)-Catalyzed Stereoinvertive Glycosylation with Primal GlycosylJournal of the American Chemical Society · 2024Article
- On the gold(I)-catalyzed enantioselective addition of indole to diphenylallene via anion-binding catalysis.Tetrahedron letters · 2024Article
- Intramolecular chalcogen bonding activated SuFEx click chemistry for efficient organic-inorganic linking.Nature communications · 2024Article
- Synergistically activating nucleophile strategy enabled organocatalytic asymmetric P-addition of cyclic imines.Chemical science · 2024Article
- Bicarbonate-binding catalysis for the enantioselective desymmetrization of keto sulfonium salts.Nature communications · 2024Article
- Redox-neutral α-functionalization of pyrrolidines: facile access to α-aryl-substituted pyrrolidines.RSC advances · 2024Article
- Catalytic Asymmetric Difluoroalkylation Using In Situ Generated Difluoroenol Species as the Privileged Synthon.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides.Journal of the American Chemical Society · 2023Article
- Article
- Exploring Structure-Function Relationships of Aryl Pyrrolidine-Based Hydrogen-Bond Donors in Asymmetric Catalysis Using Data-Driven Techniques.ACS catalysis · 2022Article
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4 authors at 1 institution in 1 country.
Funding
Abstract
Small-molecule dual hydrogen-bond (H-bond) donors such as ureas, thioureas, squaramides, and guanidinium ions enjoy widespread use as effective catalysts for promoting a variety of enantioselective reactions. However, these catalysts are only weakly acidic and therefore require highly reactive electrophilic substrates to be effective. We introduce here a mode of catalytic activity with chiral H-bond donors that enables enantioselective reactions of relatively unreactive electrophiles. Squaramides are shown to interact with silyl triflates by binding the triflate counterion to form a stable, yet highly Lewis acidic, complex. The silyl triflate-chiral squaramide combination promotes the generation of oxocarbenium intermediates from acetal substrates at low temperatures. Enantioselectivity in nucleophile additions to the cationic intermediates is then controlled through a network of noncovalent interactions between the squaramide catalyst and the oxocarbenium triflate.
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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.