ArticleAngewandte Chemie (International ed. in English)2017
Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Synthesis and Application of Bioactive N-Functionalized Aziridines.Angewandte Chemie (International ed. in English) · 2025Review
- Recent Developments in Catalytic Asymmetric Aziridination.Topics in current chemistry (Cham) · 2025Review
- PotassiumChemical science · 2025Article
- α-Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source.ChemistryOpen · 2024Review
- Catalytic stereoselective Mannich-type reactions for construction of fluorinated compounds.Molecular diversity · 2022Review
- 3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches.International journal of molecular sciences · 2021Review
- Recent advances and prospects in the Zn-catalysed Mannich reaction.RSC advances · 2021Review
- Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.Chemical science · 2018Article
- CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines.Journal of the American Chemical Society · 2017Article
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3 authors.
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Abstract
Herein, we report a Zn-ProPhenol catalyzed aza-Darzens reaction using chlorinated aromatic ketones as nucleophilic partners for the efficient and enantioselective construction of complex trisubstituted aziridines. The α-chloro-β-aminoketone intermediates featuring a chlorinated tetrasubstituted stereocenter can be isolated in high yields and selectivities for further derivatization. Alternatively, they can be directly transformed to the corresponding aziridines in a one-pot fashion. Of note, the reaction can be run on gram-scale with low catalyst loading without impacting its efficiency. Moreover, this methodology was extended to α-bromoketones which are scarcely used in enantioselective catalysis because of their sensitivity and lack of accessibility.
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