ArticleAngewandte Chemie (International ed. in English)2017
Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Construction of Vicinal Quaternary Centers via Ru-Catalyzed Enantiospecific Allylic Substitution with Lithium Ester Enolates.Journal of the American Chemical Society · 2024Article
- Iridium-catalyzed enantioselective alkynylation and kinetic resolution of alkyl allylic alcohols.Chemical science · 2022Article
- Hydroxy-directed iridium-catalyzed enantioselective formal β-C(spChemical science · 2022Article
- Iridium-catalyzed enantioselective olefinic C(spChemical science · 2021Article
- Article
- Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal.Angewandte Chemie (International ed. in English) · 2020Article
- Catalytic Asymmetric Synthesis of Cyclohexanes by Hydrogen Borrowing Annulations.Angewandte Chemie (International ed. in English) · 2019Article
- Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins.Chemical science · 2018Article
- Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis.Journal of the American Chemical Society · 2018Article
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2 authors.
Funding
Abstract
Enantioselective allylic substitution with enolates derived from aliphatic esters under mild conditions remains challenging. Herein we report iridium-catalyzed enantioselective allylation reactions of silyl ketene acetals, the silicon enolates of esters, to form products containing a quaternary carbon atom at the nucleophile moiety and a tertiary carbon atom at the electrophile moiety. Under relatively neutral conditions, the allylated aliphatic esters were obtained with excellent regioselectivity and enantioselectivity. These products were readily converted into primary alcohols, carboxylic acids, amides, isocyanates, and carbamates, as well as tetrahydrofuran and γ-butyrolactone derivatives, without erosion of enantiomeric purity.
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