ArticleJournal of the American Chemical Society2022
Catalytic Enantioselective α-Alkylation of Amides by Unactivated Alkyl Electrophiles.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Recent progress on Ni-catalysed alkyl-alkyl cross-coupling enabled by asymmetric hydrofunctionalization of alkenes.Chemical science · 2026Review
- Iridium-Catalyzed Stereoselective α-Alkylation of α-Hydroxy Ketones with Minimally Polarized Alkenes.Journal of the American Chemical Society · 2026Article
- Selective isomerization of 2,3-disubstituted butanediacetal esters and thioesters using lithium and sodium enolates: effects of bases and additives on stereoselectivity.Frontiers in chemistry · 2026Article
- Stereospecific cross-coupling reactions: Programmed assembly of chiral molecules by reaction of chiral reagents.Science advances · 2025Review
- Nickel-Catalyzed Asymmetric α-Alkenylations of Acyclic Amides that Provide Tertiary Stereocenters.Journal of the American Chemical Society · 2025Article
- Revitalizing reformatsky reagent for catalyst-free direct alkylation with unactivated alkyl halides.Nature communications · 2025Article
- β-Quaternary α-Amino Acids via Iridium-Catalyzed Branched and Enantioselective Hydroalkylation of 1,1-Disubstituted Styrenes.Angewandte Chemie (International ed. in English) · 2025Article
- α-Amido Sulfonium Salts Provide a Platform for Photocatalytic Metal-Free Carbon-Carbon Bond Formation in Amides.ACS catalysis · 2025Article
- Iridium-Catalyzed Stereocontrolled C(spJournal of the American Chemical Society · 2025Article
- CFNature communications · 2025Article
- Copper(I)-Catalyzed Enantioselective α-Alkylation of 2-Acylimidazoles.Journal of the American Chemical Society · 2024Article
- Highly Enantioselective Decarboxylative Difluoromethylation.Journal of the American Chemical Society · 2024Article
- A directed enolization strategy enables by-product-free construction of contiguous stereocentres en route to complex amino acids.Nature chemistry · 2024Article
- Harnessing Sulfur(VI) Fluoride Exchange Click Chemistry and Photocatalysis for Deaminative Benzylic Arylation.ACS catalysis · 2023Article
- Ni-Electrocatalytic Enantioselective Doubly Decarboxylative C(spJournal of the American Chemical Society · 2023Article
- Ligand-enabled Ni-catalysed enantioconvergent intermolecular Alkyl-Alkyl cross-coupling between distinct Alkyl halides.Nature communications · 2023Article
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Authors and funding
3 authors.
Funding
Abstract
Carbonyl groups that bear an α stereocenter are commonly found in bioactive compounds, and intense effort has therefore been dedicated to the pursuit of stereoselective methods for constructing this motif. While the chiral auxiliary-enabled coupling of enolates with alkyl electrophiles represented groundbreaking progress in addressing this challenge, the next advance in the evolution of this enolate-alkylation approach would be to use a chiral catalyst to control stereochemistry. Herein we describe the achievement of this objective, demonstrating that a nickel catalyst can accomplish enantioselective intermolecular alkylations of racemic Reformatsky reagents with unactivated electrophiles; the resulting α-alkylated carbonyl compounds can be converted in one additional step into a diverse array of ubiquitous families of chiral molecules. Applying a broad spectrum of mechanistic tools, we have gained insight into key intermediates (including the alkylnickel(II) resting state) and elementary steps of the catalytic cycle.
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