ArticleNature communications2023
Copper(I)-catalyzed asymmetric alkylation of α-imino-esters.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 21 citations in OpenAlex.
- Asymmetric α-Alkylation With Activated and Unactivated Electrophiles by a Highly Productive and Recyclable Lewis Acid/Imidazolium Catalyst.Angewandte Chemie (International ed. in English) · 2026Article
- Copper-Catalyzed Enantioselective Intra- and Intermolecular Desymmetrization of Azetidiniums by Carbon Nucleophiles.Journal of the American Chemical Society · 2025Article
- Photoenolization ofJournal of the American Chemical Society · 2025Article
- Copper(I)-Catalyzed Enantioselective α-Alkylation of 2-Acylimidazoles.Journal of the American Chemical Society · 2024Article
- Enhancing the Efficacy of Chiral Ligands and Catalysts: Siloxane-Substituted Oxazoline Ferrocenes as Next-Generation Candidates.Molecules (Basel, Switzerland) · 2024Review
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Asymmetric alkylation of enolates is one of the most direct and important reactions to prepare α-chiral carbonyl compounds. Except for the classical methods that rely on the use of chiral auxiliaries, asymmetric catalysis emerged as a powerful tool, especially asymmetric phase-transfer catalysis. However, in the field of transition metal catalysis, only limited success with asymmetric alkylation of enolates was achieved. Hereby, we disclose a copper(I)-catalyzed asymmetric alkylation of α-imino-esters with various alkyl halides, including allyl bromides, propargyl bromide, benzyl bromides, α-bromo carbonyl compounds, and alkyl iodides. Both linear and cyclic α-imino-esters serve as competent pronucleophiles in the alkylation, which affords α-amino acid derivatives bearing either a trisubstituted or a tetrasubstituted stereogenic carbon center in high to excellent enantioselectivity. Control experiments indicate that the α-imino-ester is activated by a chiral copper(I)-phosphine complex through coordination, thus enabling facile deprotonation to provide a stabilized copper(I)-enolate in the presence of a mild base. Finally, the mildly basic nature allows the asymmetric alkylation of chiral dipeptides with excellent both chemo- and enantioselectivities.
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Registered trials
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