ArticleJournal of the American Chemical Society2020
Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Modular assembly of chiral amino acid derivatives and peptides from commonly available feedstocks.Nature communications · 2025Article
- From Reagent to Catalyst: Dispersion-Driven Design of a General Asymmetric Transfer Hydrogenation Catalyst.Journal of the American Chemical Society · 2025Article
- Brønsted Acid-Catalyzed, Asymmetric Allenoate Claisen Reaction.The Journal of organic chemistry · 2024Article
- Computational Library Enables Pattern Recognition of Noncovalent Interactions and Application as a Modern Linear Free Energy Relationship.The Journal of organic chemistry · 2024Article
- Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis.Beilstein journal of organic chemistry · 2024Review
- Article
- Enantioselective alkylative cross-coupling of unactivated aromatic C-O electrophiles.Nature communications · 2022Article
- Molecular insights into chirality transfer from double axially chiral phosphoric acid in a synergistic enantioselective intramolecular amination.Chemical science · 2022Article
- Identifying the true origins of selectivity in chiral phosphoric acid catalyzedChemical science · 2021Article
- Data Science Meets Physical Organic Chemistry.Accounts of chemical research · 2021Article
- London Dispersion Interactions Rather than Steric Hindrance Determine the Enantioselectivity of the Corey-Bakshi-Shibata Reduction.Angewandte Chemie (International ed. in English) · 2021Article
- Interrogation of 2,2'-Bipyrimidines as Low-Potential Two-Electron Electrolytes.Journal of the American Chemical Society · 2021Article
- Catalytic Enantioselective Synthesis of Difluorinated Alkyl Bromides.Journal of the American Chemical Society · 2020Article
- Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling.Angewandte Chemie (International ed. in English) · 2020Article
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7 authors.
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Abstract
Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95% ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na
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