ArticleNature communications2015
Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis.
Article in Nature communications, 2015. 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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11 citing papers in PubMed, 72 citations in OpenAlex.
- Accessing acyclic vicinal tetrasubstituted stereocenters via biomimetic Cu/squaramide cooperative catalysed asymmetric Mannich reactions.Nature communications · 2025Article
- Nucleophilic addition of bulk chemicals with imines using N-functionalized hydroxylamine reagents as precursors.Nature communications · 2025Article
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- Intermolecular Hydroalkoxylation and Hydrocarboxylation of 2-Azadienes with High Efficiency.The Journal of organic chemistry · 2023Article
- Organocatalytic Enantioselective Michael Reaction of Aminomaleimides with Nitroolefins Catalyzed by Takemoto's Catalyst.Molecules (Basel, Switzerland) · 2022Article
- H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters.Molecules (Basel, Switzerland) · 2022Article
- Solvent-free synthesis of propargylamines: an overview.RSC advances · 2021Review
- Metal-free multicomponent approach for the synthesis of propargylamine: a review.RSC advances · 2021Review
- Direct asymmetric N-propargylation of indoles and carbazoles catalyzed by lithium SPINOL phosphate.Nature communications · 2020Article
- Urea-Derivative Catalyzed Enantioselective Hydroxyalkylation of Hydroxyindoles with Isatins.Molecules (Basel, Switzerland) · 2019Article
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Authors and funding
7 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Propargylamines are important intermediates for the synthesis of polyfunctional amino derivatives and natural products and biologically active compounds. The classic method of synthesizing chiral propargylamines involves the asymmetric alkynylation of imines. Here, we report a significant advance in the catalytic asymmetric Mannich-type synthesis of propargylamines through catalytic asymmetric addition of carbon nucleophiles to C-alkynyl imines, culminating in a highly syn-selective catalytic asymmetric Mannich reaction of C-alkynyl imines that provide syn-configured propargylamines with two adjacent stereogenic centres and a transition metal-free organocatalytic asymmetric approach to β-alkynyl-β-amino acids with high efficiency and practicality, via a chiral Brønsted base-catalysed asymmetric Mannich-type reaction of in situ generated challenging N-Boc C-alkynyl imines from previously unreported C-alkynyl N-Boc-N,O-acetals, with α-substituted β-keto esters and less-acidic malonate (thio)esters as nucleophiles, respectively. A catalytic activation strategy is also disclosed, which may have broad implications for use in catalysis and synthesis.
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