ArticleNature communications2019
Chiral donor-acceptor azetines as powerful reactants for synthesis of amino acid derivatives.
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 5 papers.
What it found
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Who cites it
5 citing papers in PubMed, 27 citations in OpenAlex.
- Enantioselective Synthesis of 2,3-Disubstituted Azetidines via Copper-Catalyzed Boryl Allylation of Azetines.Journal of the American Chemical Society · 2025Article
- Dirhodium-Catalyzed Enantioselective Synthesis of Difluoromethylated Cyclopropanes via Enyne Cycloisomerization.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Catalytic 4-exo-dig carbocyclization for the construction of furan-fused cyclobutanones and synthetic applications.Nature communications · 2023Article
- New strategies for the synthesis of 1- and 2-azetines and their applications as value-added building blocks.Organic & biomolecular chemistry · 2022Review
- Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.Molecules (Basel, Switzerland) · 2022Review
Corrections and comments
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Coupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon-oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereocontrol, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor-acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantiopurity of the original azetine.
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Registered trials
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