ArticleACS catalysis2021
Robust, Enantioselective Construction of Challenging, Biologically Relevant Tertiary Ether Stereocenters.
Article in ACS catalysis, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- One-Pot Regio- and Diastereoselective Gold-Catalyzed Propargylation of in Situ Activated Chromones and Consecutive Cyclization.Organic letters · 2024Article
- Insights into the Regioselectivity of Metal-Catalyzed Aryne Reactions.Synlett : accounts and rapid communications in synthetic organic chemistry · 2024Article
- Enantioselective Copper-Catalyzed Alkynylation of Quinolones Using Chiral P,N Ligands.The Journal of organic chemistry · 2024Article
- Copper-catalyzed C2-selective alkynylation of chromones via 1,4-conjugate addition.Molecular diversity · 2024Article
- Highly Enantioselective Catalytic Alkynylation of Quinolones: Substrate Scope, Mechanistic Studies, and Applications in the Syntheses of ChiralACS catalysis · 2023Article
- Phomoxanthone A Targets ATP Synthase.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Dearomatization of benzopyrylium triflates with sulfoxonium ylides.Chemical communications (Cambridge, England) · 2022Article
- Enantioselective Dearomative Alkynylation of Chromanones: Opportunities and Obstacles.Synthesis · 2022Article
- Asymmetric synthesis of chromanone lactonesChemical science · 2022Article
- Cu(I)-Catalyzed Alkynylation of Quinolones.Organic letters · 2022Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
A robust, catalytic enantioselective method to construct challenging, biologically relevant, tertiary ether stereocenters has been developed. The process capitalizes on readily accessible bis(oxazoline) ligands to control the facial selectivity of the addition of copper acetylides to benzopyrylium triflates, reactive species generated in situ. Up to 99% enantiomeric excesses are achieved with a broad substrate scope. Using density functional theory (DFT) calculations, the origin of the experimentally observed enantiocontrol was attributed to additional non-covalent interactions observed in the transition state leading to the major enantiomer, such as π-stacking. The resultant substrates have direct applications in the synthesis of naturally occurring bioactive chromanones and tetrahydroxanthones.
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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.