ArticleChemical science2013
Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals.
Article in Chemical science, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Asymmetric synthesis of alkyl fluoridesGreen chemistry : an international journal and green chemistry resource : GC · 2026Article
- New Strategies for the Functionalization of Carbonyl Derivatives via α-Umpolung: From Enolates to Enolonium Ions.Accounts of chemical research · 2023Article
- 2-Fluoroenones via an Umpolung Morita-Baylis-Hillman Reaction of Enones.Organic letters · 2023Article
- Catalytic Asymmetric Fluorination of Copper Carbene Complexes: Preparative Advances and a Mechanistic Rationale.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- The Fascinating Chemistry of α-Haloamides.ChemistryOpen · 2020Review
- NHC-catalyzed atropoenantioselective synthesis of axially chiral biaryl amino alcohols via a cooperative strategy.Nature communications · 2019Article
- α-Fluorination of carbonyls with nucleophilic fluorine.Nature chemistry · 2019Article
- Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes.Chemical science · 2018Article
- EnantioselectiveChemical science · 2017Article
- Stereoelectronic basis for the kinetic resolution of N-heterocycles with chiral acylating reagents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The scope of the NHC-redox amidation has been expanded to include a variety of α,β-unsaturated aldehydes, including α-fluoro α,β-unsaturated aldehydes which give rise to enantioenriched α-fluoroamides in good to excellent yield and enantioselectivity (up to 97% ee). Enantioenriched amines may be elaborated to either diastereomer of the product in high diastereoselectivity (up to 99:1). Functionalization of the amide products to amines and fluorohydrins is also demonstrated with retention of enantioenrichment at the fluorine stereocenter.
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Registered trials
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