ArticleNature communications2019
Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
What it found
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Who cites it
10 citing papers in PubMed.
- Formation of Vicinal Secondary and All-Carbon Quaternary Stereocenters in Enantioenriched Diazenes via Branched-Selective Pd-Catalyzed Allylic Alkylation.Tetrahedron letters · 2025Article
- Stereospecific positional alkene isomerization enables bidirectional central-to-axial chirality transfer.Nature communications · 2025Article
- Modular access to chiral bridged piperidine-γ-butyrolactones via catalytic asymmetric allylation/aza-Prins cyclization/lactonization sequences.Nature communications · 2024Article
- Stereodivergent synthesis of α-fluoro α-azaaryl γ-butyrolactonesFundamental research · 2024Article
- Vicinal stereocentersChemical science · 2023Article
- Recent advances in metal-catalysed asymmetric sigmatropic rearrangements.Chemical science · 2022Review
- Stereodivergent synthesis of enantioenriched azepino[3,4,5-Chemical science · 2022Article
- Stereodivergent synthesisChemical science · 2021Article
- Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivativesChemical science · 2020Article
- Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.Organic letters · 2020Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The efficient construction of enantiomerically enriched molecules from simple starting materials via catalytic asymmetric synthesis strategies is a key challenge in synthetic chemistry. Metallated azomethine ylides are commonly-used synthons for the preparation of N-heterocycles and α-amino acids. Remarkably, to date, the utilization of azomethine ylides for the facile access to chiral amines has proven elusive. Here, we report that a synergistic Cu/Ir-catalytic system combined with careful tuning of the steric congestion can be used to convert aldimine esters to a variety of chiral homoallylic amines via a cascade allylation/2-aza-Cope rearrangement. The elucidation of the distinct effects of each stereogenic center of the allylation intermediates on the stereochemical outcome and chirality transfer in the rearrangement further guided the selection of catalysts combination.
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Registered trials
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