ArticleNature communications2019
An umpolung strategy to react catalytic enols with nucleophiles.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 30 citations in OpenAlex.
- α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation.Angewandte Chemie (International ed. in English) · 2022Article
- An Expedient Method for the Umpolung Coupling of Enols with Heteronucleophiles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones.Angewandte Chemie (International ed. in English) · 2021Article
- Stereospecific Isomerization of Allylic Halides via Ion Pairs with Induced Noncovalent Chirality.Organic letters · 2020Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The selective synthesis of α-functionalized ketones with two similar enolizable positions can be accomplished using allylic alcohols and iridium(III) catalysts. A formal 1,3-hydrogen shift on allylic alcohols generates catalytic iridium-enolates in a stereospecific manner, which are able to react with electrophiles to yield α-functionalized ketones as single constitutional isomers. However, the employment of nucleophiles to react with the nucleophilic catalytic enolates in this chemistry is still unknown. Herein, we report an umpolung strategy for the selective synthesis of α-alkoxy carbonyl compounds by the reaction of iridium enolates and alcohols promoted by an iodine(III) reagent. Moreover, the protocol also works in an intramolecular fashion to synthesize 3(2H)-furanones from γ-keto allylic alcohols. Experimental and computational investigations have been carried out, and mechanisms are proposed for both the inter- and intramolecular reactions, explaining the key role of the iodine(III) reagent in this umpolung approach.
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Registered trials
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