ArticleNature chemistry2023
Modular and diverse synthesis of amino acids via asymmetric decarboxylative protonation of aminomalonic acids.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- CChemistry, an Asian journal · 2026Article
- Enantioselective Electrocatalytic Hydrogenation of α,β-Unsaturated Esters and Allylic Alcohols.Nature communications · 2026Article
- Ultrafast charge-generation dynamics through interfacial energetic modulation for high-performance single-component organic photovoltaics with 14.8% efficiency.Nature communications · 2026Article
- Printable Newtonian fluid photocatalysts for scale-up solar CONature communications · 2026Article
- Amino-Modified Mesoporous Bioactive Glass Adsorbed with Osteopontin Enhances Osteogenic Differentiation and Matrix Mineralization via the Erk1/2 Signaling Pathway.Journal of functional biomaterials · 2026Article
- Radical defluoroallylation of polyfluoroalkyl compounds with alkenes via synergistic photoredox/cobalt catalysis.Nature communications · 2026Article
- Multiple hydrogen bonding enables large-area doped phosphorescent glasses with robust stability and high-temperature afterglow.Nature communications · 2026Article
- Photoenolization ofJournal of the American Chemical Society · 2025Article
- Biocatalytic Synthesis of α-Amino Esters via Nitrene C-H Insertion.Journal of the American Chemical Society · 2024Article
- The crystal structure of the ammonium salt of 2-aminomalonic acid.Acta crystallographica. Section C, Structural chemistry · 2024Article
- Enantioselective organocatalytic strategies to access noncanonical α-amino acids.Chemical science · 2024Review
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Authors and funding
4 authors.
Funding
Abstract
Stereoselective protonation is a challenge in asymmetric catalysis. The small size and high rate of transfer of protons mean that face-selective delivery to planar intermediates is hard to control, but it can unlock previously obscure asymmetric transformations. Particularly, when coupled with a preceding decarboxylation, enantioselective protonation can convert the abundant acid feedstocks into structurally diverse chiral molecules. Here an anchoring group strategy is demonstrated as a potential alternative and supplement to the conventional structural modification of catalysts by creating additional catalyst-substrate interactions. We show that a tailored benzamide group in aminomalonic acids can help build a coordinated network of non-covalent interactions, including hydrogen bonds, π-π interactions and dispersion forces, with a chiral acid catalyst. This allows enantioselective decarboxylative protonation to give α-amino acids. The malonate-based synthesis introduces side chains via a facile substitution of aminomalonic esters and thus can access structurally and functionally diverse amino acids.
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