ArticleJournal of the American Chemical Society2015
Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Enantioselective Pd-Catalyzed Electrochemical Dearomative Allylation of Tropones: Construction of All-C Quaternary Stereocenters.Organic letters · 2026Article
- Enantioselective electrochemical nickel-catalyzed vinylogous radical reactions.Science advances · 2025Article
- Iridium-Catalyzed Enantioselective Vinylogous and Bisvinylogous Allenylic Substitution.JACS Au · 2024Article
- Catalytic asymmetric defluorinative allylation of silyl enol ethers.Chemical science · 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
- Palladium-catalyzed asymmetric allylic alkylation (AAA) with alkyl sulfones as nucleophiles.Chemical science · 2021Article
- The Allylic Alkylation of Ketone Enolates.ChemistryOpen · 2020Review
- Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis.Journal of the American Chemical Society · 2018Article
- Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.Angewandte Chemie (International ed. in English) · 2017Article
- Scalable synthesis of enaminones utilizing Gold's reagents.Tetrahedron, asymmetry · 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 Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.Angewandte Chemie (International ed. in English) · 2016Article
- Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement.Journal of the American Chemical Society · 2016Article
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2 authors.
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Abstract
The enol silanes of vinylogous esters and amides are classic dienes for Diels-Alder reactions. Here, we report their reactivity as nucleophiles in Ir-catalyzed, enantioselective allylic substitution reactions. A variety of allylic carbonates react with these nucleophiles to give allylated products in good yields with high enantioselectivities and excellent branched-to-linear ratios. These reactions occur with KF or alkoxide as the additive, but mechanistic studies suggest that these additives do not activate the enol silanes. Instead, they serve as bases to promote the cyclometalation to generate the active Ir catalyst. The carbonate anion, which was generated from the oxidative addition of the allylic carbonate, likely activates the enol silanes to trigger their activity as nucleophiles for reactions with the allyliridium electrophile. The synthetic utility of this method was illustrated by the synthesis of the anti-muscarinic drug, fesoterodine.
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