ArticleJournal of the American Chemical Society2016
Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Organocatalytic aromatization-promoted umpolung reaction of imines.Nature chemistry · 2024Article
- Nickel-catalyzed enantioselective vinylation of aryl 2-azaallyl anions.Chemical science · 2021Article
- Strategies for the Catalytic Enantioselective Synthesis ofACS catalysis · 2020Article
- Synthesis of chiral anti-1,2-diamine derivatives through copper(I)-catalyzed asymmetric α-addition of ketimines to aldimines.Nature communications · 2020Article
- Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.Organic letters · 2020Article
- Pd-Catalyzed Allylation of Imines to Access α-CFEuropean journal of organic chemistry · 2019Article
- 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.Synlett : accounts and rapid communications in synthetic organic chemistry · 2019Article
- Synthesis of α-CFOrganic & biomolecular chemistry · 2019Article
- Direct Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Esters/Lactones via Umpolung Strategy.The Journal of organic chemistry · 2019Article
- Palladium-Catalyzed Synthesis ofACS catalysis · 2019Article
- Intramolecular Umpolung Synthesis of Exocyclic β-Amino Alcohols through Decarboxylative Amination.ACS omega · 2018Article
- Origin of and a Solution for Uneven Efficiency by Cinchona Alkaloid-Derived, Pseudoenantiomeric Catalysts for Asymmetric Reactions.Journal of the American Chemical Society · 2018Article
- Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives.Angewandte Chemie (International ed. in English) · 2018Article
Corrections and comments
- Erratum issued
Authors and funding
4 authors.
Funding
Abstract
The first direct catalytic asymmetric synthesis of γ-amino ketones was realized by the development of a highly diastereoselective and enantioselective C-C bond-forming umpolung reaction of imines and enones under the catalysis of a new cinchona alkaloid-derived phase-transfer catalyst. In a loading ranging from 0.02 to 2.5 mol %, the catalyst activates a broad range of trifluoromethyl imines and aldimines as nucleophiles to engage in chemo-, regio-, diastereo- and enantioselective C-C bond-forming reactions with acyclic and cyclic enones, thereby converting these readily available prochiral starting materials into highly enantiomerically enriched chiral γ-amino ketones in synthetically useful yields. Enabled by this unprecedented umpolung reaction of imines, conceptually new and concise routes were developed for the asymmetric synthesis of nitrogen-heterocycles such as pyrrolidines and indolizidines.
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