6975-17-3Relevant academic research and scientific papers
HClO4·SiO2-mediated improved isomerization of glycidic esters to α-hydroxy-β,γ -unsaturated esters: Application in the formal synthesis of (R)-Baclofen and β-phenyl GABA analogues
Basak, Ranjan,Dharuman, Suresh,Reddy, Y. Suman,Doddi, Venkata Ramana,Vankar, Yashwant D.
supporting information; experimental part, p. 325 - 327 (2012/06/01)
An efficient isomerization of glycidic esters to corresponding allylic alcohols, viz. α-hydroxy-β,γ -unsaturated esters has been brought about using HClO4·SiO2. Five of these allylic alcohols underwent selective SN2' nucleophilic substitution to generate γ-azido-α,β-unsaturated esters which were readily converted to an antispastic drug Baclofen and four other β-phenyl GABA analogues.
The synthesis of solvent-free glycidic esters from diazoesters and carbonyl compounds catalysed by lanthanide trifiates
Curini, Massimo,Epifano, Francesco,Marcotullio, Maria Carla,Rosati, Ornelio
, p. 1562 - 1565 (2007/10/03)
The results of the reaction between ethyl diazoacetate and carbonyl compounds catalysed by lanthanide triflates are described. Aldehydes, and α-unsubstituted and α-monosubstituted cyclohexanones react to give the selective formation of α,β-epoxy esters (g
Mechanism of formation of 5,5-cyclopentamethylene-3,4-dicarbethoxyfuranone-2 from ethyl β,β-pentamethyleneglycidate and diethyl malonate
Gedam, Hema S.,Bagavant, G.
, p. 1278 - 1280 (2007/10/02)
An O18 isotope study of the reaction of glycidate (1c) with diethyl malonate leading to a furanone diester (2d) reveal that there is a ring cleavage followed by an intramolecular cyclisation.Isotopic evidence for the Darzen's reaction is given.The glycidate (1c) does not undergo cleavage with benzylamine, however with hydrogen chloride a chlorohydrin through the cleavage of the epoxide ring is obtained.
α-Bromo-, α-chloro-, and α-trimethylsilyl-zinc ester enolates. New and universal Reformatsky-type Darzens and Peterson reactions
Fuerstner, Alois
, p. C33 - C36 (2007/10/02)
Low temperature reactions of ethyl dihaloacetates with carbonyl compounds in the presence of zinc/silver-graphite give α-halo-β-hydroxyalkanoates, which are readily converted into glycidates by base.Unser the same conditions ethyl(bromo)(trimethylsilyl) acetate with aldehydes and ketones forms α,β-unsaturated esters by a Reformatsky-Peterson reaction combination.
Methode generale d'obtention des α-ceto esters β-fluores
Ourari, Ali,Condom, Roger,Guedj, Roger
, p. 2707 - 2710 (2007/10/02)
A general method of synthesis of 3-alkyl (or aryl) 3-fluoro 2-oxo esters is described.The opening of glycidic esters with HF-pyridine (70percent w/w) followed by oxidation with Jones reagent, give the corresponding derivatives of fluoropyruvic esters in good yields.
NEW SYNTHETIC ROUTES TO β-FLUORO β-PHENYLLACTIC ACID DERIVATIVES AND Β-FLUOROCYANOHYDRINS
Ayi, A. I.,Remli, M.,Condom, R.,Guedj, R.
, p. 565 - 580 (2007/10/02)
Alkyl phenyl 2,3-epoxycarboxylates from the well-known Darzens glycidic esters synthesis react under very mild conditions with pyridinium-poly-hydrogen fluoride to give corresponding 3-fluoro 3-phenyllactates in almost quantitative yields with a high regio and stereoselectivity.This method can be applied succesfully to other flycidic derivatives: glycidoamides, glycidonitriles, glycidoiminoesters...The spectrometric properties (IR, NMR) are presented.
