204510-36-1

Upstream product

• 1522-41-4 ethyl-2-fluoroacetoacetate 
• 100-39-0 benzyl bromide 
• 141-97-9 ethyl acetoacetate 
• 620-79-1 Ethyl 2-benzylacetoacetate 

Downstream Products

• 99687-75-9 3-fluoro-4-phenylbutan-2-one 

Relevant academic research and scientific papers

Fast, solvent-free and highly enantioselective fluorination of β-keto esters catalyzed by chiral copper complexes in a ball mill

A fast and highly enantioselective fluorination of β-keto esters catalyzed by diphenylamine linked bis(oxazoline)-Cu(OTf)2 complexes under solvent-free conditions has been developed using a planetary ball mill. High yields, high enantioselectivities and shorter reaction times were achieved with low catalyst loading.

Development of the titanium-TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

Titanium-based Lewis acids catalyze the α-fluorination of β-ketoesters by electrophilic N-F-fluorinating reagents. Asymmetric catalysis with TADDOLato-titanium(IV) dichloride (TADDOL = α,α, α',α'-tetraaryl-(1,3-dioxolane-4,5-diyl)-dimethanol) Lewis acids

Towards greener fluorine organic chemistry: Direct electrophilic fluorination of carbonyl compounds in water and under solvent-free reaction conditions

Selective and efficient fluorination of organic 1,3-dicarbonyl compounds was achieved using the electrophilic fluorinating reagents Selectfluor TM F-TEDA-BF4 (1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis-tetrafluoroborate) in aqueous medium or AccufluorTM NFSi (N-fluorobenzenesulfonimide) under solvent-free reaction conditions (SFRC). Under both reaction conditions cyclic 1,3-dicarbonyl compounds were transformed into 2-fluoro-substituted derivatives and acyclic analogues into 2,2-difluoro-substituted compounds, while the reactions of 1-trifluoromethyl-substituted 1,3-dicarbonyls in water resulted in the formation of 2,2-difluoro-3,3-dihydroxy-1-one derivatives. The reactivity of the starting material in water was found to be dependent on its enolizability, hydrophobic interactions and aggregate state at the reaction temperature. Reactions under SFRC proceeded in the molten eutectic phase of the reactants. The technique of competitive reactivity was used in order to evaluate and better understand the effects of reaction conditions on the course of these reactions.

2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination

A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2′-bipyridine-3,3′-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model β-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands.

Alkylation and decarboxylation of ethyl 2-fluoro-3-oxobutanoate as a route to functionalised α-fluoro-ketones

Alkylation and decarboxylation of α-fluoro-β-ketoesters such as ethyl 2-fluoro-3-oxobutanoate offers a versatile route to a range of fluoro-ketoalkenes, demonstrating the synthetic utility of using α-fluoro-β-ketoesters as synthons for the preparation of synthetically more sophisticated selectively fluorinated systems.