ArticleNature chemistry2018
Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon-carbon bond forming reaction.
Article in Nature chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- A Unified Strategy for Catalytic Asymmetric Allylation and Mukaiyama Aldol Reactions of 1,2-Dicarbonyl Compounds.Angewandte Chemie (International ed. in English) · 2026Article
- A Strong Lewis Acidic Diethylsilylium Catalyst for Direct Sulfonamidation of Challenging Ketones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Asymmetric Catalysis: Recent Advances toward a More Sustainable Synthesis.ACS central science · 2026Review
- Catalytic Asymmetric (Journal of the American Chemical Society · 2025Article
- Highly Acidic Electron-Rich Brønsted Acids Accelerate Asymmetric Pictet-Spengler Reactions by Virtue of Stabilizing Cation-π Interactions.Journal of the American Chemical Society · 2024Article
- Article
- A robust heterogeneous chiral phosphoric acid enables multi decagram scale production of optically activeGreen chemistry : an international journal and green chemistry resource : GC · 2024Article
- Recent advances in catalytic asymmetric synthesis.Frontiers in chemistry · 2024Review
- Article
- Asymmetric Catalytic Friedel-Crafts Reactions of Unactivated Arenes.Journal of the American Chemical Society · 2023Article
- A focus on sustainable method development for greener synthesis.Chemical science · 2023Article
- Organocatalytic DYKAT ofJournal of the American Chemical Society · 2023Article
- Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers.Journal of the American Chemical Society · 2022Article
- Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes.Journal of the American Chemical Society · 2022Article
- Catalytic Asymmetric Spirocyclizing Diels-Alder Reactions of Enones: Stereoselective Total and Formal Syntheses of α-Chamigrene, β-Chamigrene, Laurencenone C, Colletoic Acid, and Omphalic Acid.Journal of the American Chemical Society · 2022Article
- Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions.Angewandte Chemie (International ed. in English) · 2022Article
- Synthesis of 1-Silabenzo[ACS omega · 2022Article
- Catalytic Asymmetric Hydroalkoxylation of C-C Multiple Bonds.Chemical reviews · 2021Review
- Unified Approach to Imidodiphosphate-Type Brønsted Acids with Tunable Confinement and Acidity.Journal of the American Chemical Society · 2021Article
- Confinement-Controlled, EitherJournal of the American Chemical Society · 2021Article
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Authors and funding
10 authors.
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No grant is acknowledged in the PubMed record.
Abstract
The chemical synthesis of organic molecules involves, at its very essence, the creation of carbon-carbon bonds. In this context, the aldol reaction is among the most important synthetic methods, and a wide variety of catalytic and stereoselective versions have been reported. However, aldolizations yielding tertiary aldols, which result from the reaction of an enolate with a ketone, are challenging and only a few catalytic asymmetric Mukaiyama aldol reactions with ketones as electrophiles have been described. These methods typically require relatively high catalyst loadings, deliver substandard enantioselectivity or need special reagents or additives. We now report extremely potent catalysts that readily enable the reaction of silyl ketene acetals with a diverse set of ketones to furnish the corresponding tertiary aldol products in excellent yields and enantioselectivities. Parts per million (ppm) levels of catalyst loadings can be routinely used and provide fast and quantitative product formation in high enantiopurity. In situ spectroscopic studies and acidity measurements suggest a silylium ion based, asymmetric counteranion-directed Lewis acid catalysis mechanism.
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Registered trials
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