ArticleChemical science2021
Organocatalytic asymmetric synthesis of α-amino esters from sulfoxonium ylides.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 53 citations in OpenAlex.
- Catalytic Enantioselective Multicomponent Reactions of Sulfoxonium Ylides Enabled by a Formal Rearrangement-A Versatile Entry to Enantioenriched α-Sulfanyl Carbonyl Compounds.Angewandte Chemie (International ed. in English) · 2026Article
- Enantioselective Synthesis of α-Oxygenated Ketones via Organocatalytic Formal O-H Bond Insertion of Sulfonium Ylides.Journal of the American Chemical Society · 2025Article
- Molybdenum-Catalyzed Asymmetric Amination of α-Hydroxy Esters: Synthesis of α-Amino Acids.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides.Molecules (Basel, Switzerland) · 2025Review
- Dual NHC/HAT-Promoted Esterification to Access α-Aryl Glycines.Advanced synthesis & catalysis · 2025Article
- Enantioselective organocatalytic strategies to access noncanonical α-amino acids.Chemical science · 2024Review
- Bridging the information gap in organic chemical reactions.Nature chemistry · 2024Review
- Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis.Organic letters · 2023Article
- Molecular Understanding and Practical In Silico Catalyst Design in Computational Organocatalysis and Phase Transfer Catalysis-Challenges and Opportunities.Molecules (Basel, Switzerland) · 2023Review
- Visible-light-induced organocatalytic enantioselective N-H insertion of α-diazoesters enabled by indirect free carbene capture.Chemical science · 2023Article
- Synthesis of INature communications · 2022Article
- Regioselective α-addition of vinylogous α-ketoester enolate in organocatalytic asymmetric Michael reactions: enantioselective synthesis of Rauhut-Currier type products.RSC advances · 2022Article
- Organocatalytic asymmetric azidation of sulfoxonium ylides: mild synthesis of enantioenriched α-azido ketones bearing a labile tertiary stereocenter.Chemical science · 2022Article
- Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures.Organic letters · 2022Article
- Asymmetric transformations from sulfoxonium ylides.Chemical science · 2022Review
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Described here is the first organocatalytic asymmetric N-H insertion reaction of α-carbonyl sulfoxonium ylides. Without a metal catalyst, this reaction represents an attractive complement to the well-established carbene insertion reactions. As a stable surrogate of diazocarbonyl compounds, sulfoxonium ylides reacted with a range of aryl amines to provide efficient access to α-aryl glycines with excellent enantiocontrol in the presence of a suitable chiral phosphoric acid catalyst. The high stability and weak basicity of sulfoxonium ylides not only enable this protocol to be user-friendly and practically useful, but also preclude catalyst decomposition, which is crucial to the excellent amenability to electron-poor amine nucleophiles. Detailed mechanistic studies indicated that the initial protonation is reversible and the C-N bond formation is rate-determining.
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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.