6533b856fe1ef96bd12b25dd

RESEARCH PRODUCT

Reaction of lithium enediolates with perfluoroketene dithioacetals. Synthesis of α-trifluoromethyl γ-dicarboxylic acid derivatives

Jean-philippe BouillonEnrique SotocaEnrique SotocaCharles PortellaSalvador GilMargarita Parra

subject

chemistry.chemical_classificationTrifluoromethylBase (chemistry)Organic ChemistryExtraction (chemistry)chemistry.chemical_elementBiochemistryMedicinal chemistrychemistry.chemical_compoundFormal synthesisDicarboxylic acidchemistryDrug DiscoveryOrganic chemistryLithiumFluoride

description

The reaction of perfluoroketene dithioacetals with dianions of carboxylic acids proceeds through the substitution of the vinylic fluoride. The preparative value of this reaction depends strongly on the reaction and work-up conditions, the optimisation of which led to use LDA as a base and multiple extraction techniques. The overall process may be considered as a formal synthesis of α-trifluoromethyl γ-dicarboxylic acid derivatives.

https://doi.org/10.1016/j.tetlet.2004.09.081