ArticleMolecules (Basel, Switzerland)2018
Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters.
Article in Molecules (Basel, Switzerland), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide.Beilstein journal of organic chemistry · 2024Article
- Organocatalytic asymmetric azidation of sulfoxonium ylides: mild synthesis of enantioenriched α-azido ketones bearing a labile tertiary stereocenter.Chemical science · 2022Article
- Asymmetric Azidation under Hydrogen Bonding Phase-Transfer Catalysis: A Combined Experimental and Computational Study.Journal of the American Chemical Society · 2022Article
- Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions.Molecules (Basel, Switzerland) · 2021Article
- Asymmetric α-Chlorination of β-Keto Esters Using Hypervalent Iodine-Based Cl-Transfer Reagents in Combination with Cinchona Alkaloid Catalysts.European journal of organic chemistry · 2021Article
- Insight into trifluoromethylation - experimental electron density for Togni reagent I.RSC advances · 2018Article
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Authors and funding
5 authors.
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Abstract
Detailed investigations concerning the organocatalytic (asymmetric) α-azidation of prochiral β-ketoesters were carried out. It was shown that the racemic version of such a reaction can either be carried out under oxidative conditions using TMSN₃ as the azide-source with quaternary ammonium iodides as the catalysts, or by using hypervalent iodine-based electrophilic azide-transfer reagents with different organocatalysts. In addition, the latter strategy could also be carried out with modest enantioselectivities when using simple cinchona alkaloid catalysts, albeit with relatively low yields.
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