ArticleNature chemistry2024
Modular α-tertiary amino ester synthesis through cobalt-catalysed asymmetric aza-Barbier reaction.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
- Photoinduced cobalt-catalyzed enantioconvergent synthesis of 1,3-diamines via aziridine ring-opening addition.Science advances · 2026Article
- Enantioselective Vinyl Radical Addition to Aldehydes via Dual Chromium Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Emerging enzymatic strategies for the synthesis of α-tertiary amino acids.Communications chemistry · 2026Review
- Cobalt-catalyzed asymmetric three-component reductive addition of alkynes with alkyl halides and imines.Nature communications · 2026Article
- Sulfonyl-PYBOX/ErClNature communications · 2026Article
- Photo-enabled and thioamide-directed α-C(spNature communications · 2026Article
- Kinetic resolution of amino acids by phosphine oxide catalyzed enantioselective esterification.Nature communications · 2026Article
- Enantioconvergent radical addition of racemic alkyl halides to access vicinal stereocentres.Nature chemistry · 2026Article
- Modular assembly of chiral amino acid derivatives and peptides from commonly available feedstocks.Nature communications · 2025Article
- Trifluoromethylation of alkyl electrophiles withScience (New York, N.Y.) · 2025Article
- Mechanistic and Structural Analyses of Non-Heme Iron Enzyme TqaM for α-Tertiary Amino Acid Synthesis.Journal of the American Chemical Society · 2025Article
- Dinickel-catalyzed enantioselective reductive addition of imines with vinyl halides.Nature communications · 2025Article
- Diastereodivergent synthesis of multi-substituted cycloalkanes.Nature chemistry · 2025Article
- Gold-modified nanoporous silicon for photoelectrochemical regulation of intracellular condensates.Nature nanotechnology · 2025Article
- Trifluoroethanol-assisted asymmetric propargylic hydrazination to α-tertiary ethynylhydrazines enabled by sterically confined pyridinebisoxazolines.Nature communications · 2025Article
- Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides.Nature communications · 2025Article
- Biocatalytic Synthesis of α-Amino Esters via Nitrene C-H Insertion.Journal of the American Chemical Society · 2024Article
- Harnessing the potential of acyl triazoles in bifunctional cobalt-catalyzed radical cross-coupling reactions.Nature communications · 2024Article
- Metal-carbene-guided twofold cross-coupling of ethers with chromium catalysis.Nature communications · 2024Article
- Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis.JACS Au · 2024Article
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Authors and funding
13 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Unnatural chiral α-tertiary amino acids containing two different carbon-based substituents at the α-carbon centre are widespread in biologically active molecules. This sterically rigid scaffold is becoming a growing research interest in drug discovery. However, a robust protocol for chiral α-tertiary amino acid synthesis remains scarce due to the challenge of stereoselectively constructing sterically encumbered tetrasubstituted stereogenic carbon centres. Herein we report a cobalt-catalysed enantioselective aza-Barbier reaction of ketimines with various unactivated alkyl halides, including alkyl iodides, alkyl bromides and alkyl chlorides, enabling the formation of chiral α-tertiary amino esters with a high level of enantioselectivity and excellent functional group tolerance. Primary, secondary and tertiary organoelectrophiles are all tolerated in this asymmetric reductive addition protocol, which provides a complementary method for the well-exploited enantioselective nucleophilic addition with moisture- and air-sensitive organometallic reagents. Moreover, the three-component transformation of α-ketoester, amine and alkyl halide represents a formal asymmetric deoxygenative alkylamination of the carbonyl group.
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38082178What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.