54340-71-5Relevant academic research and scientific papers
Taming the carboxyl group for directed carbometalation: Observations on the use of anions, dianions and ester enolates
Desrat, Sandy,Gray, Philip J.,Penny, Matthew R.,Motherwell, William B.
supporting information, p. 8918 - 8922 (2014/07/22)
Carboxylate anions, dianions and ester enolates provide simultaneous protection and activation for directed carbometalation reactions. Advantage can be taken of the bis-carbanionic character of the intermediate for further controlled C-C bond forming reac
Regioselective ring opening and isomerization reactions of 3,4-epoxyesters catalyzed by boron trifluoride
Izquierdo, Javier,Rodriguez, Santiago,Gonzalez, Florenci V.
supporting information; experimental part, p. 3856 - 3859 (2011/09/19)
Efficient ring opening of 3,4-epoxyesters with alcohols to produce 4-alkoxy-3-hydroxyesters and their isomerization into 4-ketoesters using boron trifluoride as the catalyst are presented. Both transformations are simple and efficient methods for the synthesis of the above named synthetically useful compounds.
A practical, efficient, and atom economic alternative to the Wittig and Horner-Wadsworth-Emmons reactions for the synthesis of (E)-α,β- unsaturated esters from aldehydes
List, Benjamin,Doehring, Arno,Hechavarria Fonseca, Maria T.,Job, Andreas,Rios Torres, Ramon
, p. 476 - 482 (2007/10/03)
We describe a highly efficient new methodology for the synthesis of (E)-α,β-unsaturated esters from aldehydes. In our DMAP-catalyzed reaction, both aromatic as well as aliphatic aldehydes furnish the desired products highly regio- and stereoselectively if treated with commercially available or synthetically easily accessible malonic acid half ester. A large scale application in the synthesis of p-methoxycinnamates, which are of use as sunscreen ingredients, is described.
Palladium-Catalyzed Carbonylation of Allylamines. Synthesis of β,γ-Unsaturated Amides by One-Carbon Homologation of Allylamines
Murahashi, Shun-Ichi,Imada, Yasushi,Nishimura, Koichi
, p. 453 - 464 (2007/10/02)
Palladium-catalyzed carbonylation of allylamines under CO (50 atm) at 110 deg C proceeds highly efficiently to give the correponding β,γ-unsaturated amides.The carbonylation occurs at the less substituted carbon of allyl units to give linear amides with h
Palladium(0)-Catalyzed Alkoxycarbonylation of Allyl Phosphates and Acetates
Murahashi, Shun-Ichi,Imada, Yasushi,Taniguchi, Yuki,Higashiura, Shinya
, p. 1538 - 1545 (2007/10/02)
Palladium-catalyzed alkoxycarbonylation of allyl phosphates under CO (1 atm) at 50 deg C proceeds highly efficiently to give the corresponding β,γ-unsaturated esters.The carbonylation of geranyl phosphate ((E)-11) under CO (1 atm) at 50 deg C gave ethyl ester of homogeranic acid ((E)-12) stereoselectively.The carbonylation takes place at least substituted allylic positions with inversion of configuration.Typically, the methoxycarbonylation of cis-5-(methoxycarbonyl)-2-cyclohexen-1-yl phosphate (cis-16) gave trans-dimethyl-2-cyclohexene-1,5-dicarboxylate (trans-17) selectively.Alkoxycarbonylation of allyl acetates is performed for the first time in the presence of a catalytic amount of bromide ion.The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium(0) species to allyl acetates to give ?-allylpalladium acetate, fast ligand exchange of the acetate with bromide, insertion of carbon monoxide to give acylpalladium species, and alkoxylation.
Stereochemistry of Deconjugative Alkylation of Ester Dienolates. Stereospecific Total Synthesis of the Litsenolides
Kende, Andrew S.,Toder, Bruce H.
, p. 163 - 167 (2007/10/02)
Deconjugative protonations, alkylations, and aldol condensations of the dienolates from (Z)-2-alkenoates give the corresponding (E)-3-enoate products, whereas dienolates from (E)-2-enoates give mainly the (Z)-3-enoate products.These generalizations are exploited in stereospecific total syntheses of litsenolides A2, B2, and C2.
