ArticleAngewandte Chemie (International ed. in English)2016
Iridium-Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic α-Alkoxy Ketones.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Article
- Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction.Chemical science · 2024Article
- Experimental and Computational Studies on Cobalt(I)-Catalyzed Regioselective Allylic Alkylation Reactions.Angewandte Chemie (International ed. in English) · 2023Article
- A Catalytic Method for the Enantioselective Synthesis of α-Quaternary Ketones, α-Ketoesters and Aldehydes.Angewandte Chemie (International ed. in English) · 2023Article
- Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization.Molecules (Basel, Switzerland) · 2022Article
- The Allylic Alkylation of Ketone Enolates.ChemistryOpen · 2020Review
- Dehydration in water: frustrated Lewis pairs directly catalyzed allylization of electron-rich arenes and allyl alcohols.RSC advances · 2020Article
- Catalytic Asymmetric Allylic Amination with Isatins, Sulfonamides, Imides, Amines, andOrganic letters · 2020Article
- Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin-Derived Enol Carbonates.Advanced synthesis & catalysis · 2020Article
- An umpolung strategy to react catalytic enols with nucleophiles.Nature communications · 2019Article
- Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.Chemical science · 2019Article
- Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins.Chemical science · 2018Article
- Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.Angewandte Chemie (International ed. in English) · 2018Article
- Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis.Journal of the American Chemical Society · 2018Article
- Direct Asymmetric Alkylation of Ketones: Still Unconquered.Angewandte Chemie (International ed. in English) · 2017Review
- Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.Angewandte Chemie (International ed. in English) · 2017Article
- Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles.Angewandte Chemie (International ed. in English) · 2017Article
- Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.Journal of the American Chemical Society · 2017Article
- Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.Angewandte Chemie (International ed. in English) · 2016Article
- Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.Angewandte Chemie (International ed. in English) · 2016Article
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3 authors.
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Abstract
The asymmetric alkylation of acyclic ketones is a longstanding challenge in organic synthesis. Reported herein are diastereoselective and enantioselective allylic substitutions with acyclic α-alkoxy ketones catalyzed by a metallacyclic iridium complex to form products with contiguous stereogenic centers derived from the nucleophile and electrophile. These reactions occur between allyl methyl carbonates and unstabilized copper(I) enolates generated in situ from acyclic α-alkoxy ketones. The resulting products can be readily converted into enantioenriched tertiary alcohols and tetrahydrofuran derivatives without erosion of enantiomeric purity.
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