ArticleChemical science2022
Practical asymmetric amine nucleophilic approach for the modular construction of protected α-quaternary amino acids.
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Light-Driven Epimerization: Diastereoconvergent Synthesis of [Angewandte Chemie (International ed. in English) · 2026Article
- Enantioselective construction of cyclic quaternary stereocenters via dinuclear copper catalyzed asymmetric [3 + 2] propargylation/annulation.Nature communications · 2025Article
- Trifluoroethanol-assisted asymmetric propargylic hydrazination to α-tertiary ethynylhydrazines enabled by sterically confined pyridinebisoxazolines.Nature communications · 2025Article
- Cu-Catalyzed Asymmetric Synthesis of γ-Amino Alcohols Featuring Tertiary Carbon Stereocenters.Organic letters · 2024Article
- Enantioselective propargylic amination and related tandem sequences to α-tertiary ethynylamines and azacycles.Nature chemistry · 2024Article
- Challenges and recent advancements in the synthesis of α,α-disubstituted α-amino acids.Nature communications · 2024Review
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Authors and funding
3 authors.
Funding
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Abstract
We report the first amine nucleophilic approach for the modular construction of enantioenriched protected α-quaternary amino acids. The key to success is the use of an alcohol solvent, which makes a rationally designed COOMe-bonded Cu-allenylidene electrophilic intermediate stable enough to couple with amine nucleophiles before its decomposition. The reaction features wide functional group tolerance with high enantioselectivity, typically >90% ee, and is amenable to the modification of commercially available bioactive molecules. The resultant protected α-amino acids could be readily converted into a number of precious enantioenriched amines featuring α-hindered tertiary carbon centers, which are otherwise synthetically quite challenging, including those of α-amino aldehyde, peptides or α-vinyl amino ester with >92% ee in excellent yields. This protocol could be utilized for the synthesis of the protected bioactive α-ethylnorvaline in 3 steps, a significant advancement in comparison to an 11-step sequence reported previously.
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Registered trials
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