Search results for "carboxylation"

Competition between decarboxylation and isomerization in the C3H5O 2+ energy surface. Justification of the experimental results by molecular orbital …

1994

In constrast with recent molecular orbital calculations on the decarboxylation of O-protonated 2-oxetanone, this experimental work indicates that no decarboxylation of this cation occurs in sulphuric acid solution up to 150°C, but instead a clean isomerization to protonated acrylic acid takes place. Parallel theoretical work shows that the gas-phase model is too crude to account successfully for the experimental facts obtained in acidic media. However, the latter are well reproduced when the effect of the solvent is taken into account. The present findings do not necessarily invalidate the reaction mechanism currently accepted to explain the rate enhancement and change of stereochemistry ac…

A Simple Organocatalytic Enantioselective Synthesis of Pregabalin

2009

This paper describes a new procedure for the enantioselective synthesis of the important anticonvulsant drug Pregabalin, which shows biological properties as the (S) enantiomer only. The key step of the synthetic sequence is the Michael addition reaction of Meldrum's acid to a nitroalkene mediated by a quinidine derived thiourea. A variety of novel catalysts bearing different groups at the thiourea moiety were synthesized and tested. The most successful catalyst that incorporates a trityl substituent provided up to 75 % ee of (S)-4. The conjugate addition reaction was carried out on a multigram scale with low loadings of catalyst (10 mol-%). Moreover, the catalyst can be recycled showing th…

Electrochemical Synthesis of Aryl Methoxymethyl Ethers

2019

Recent Scientific and Technological Developments in Electrochemical Carboxylation Based on Carbon Dioxide

2010

ChemInform Abstract: Catalytic Aerobic Oxidative Decarboxylation of α-Hydroxy Acids. Methyl Mandelate as a Benzoyl Anion Equivalent.

2010

Abstract The monomeric square-planar cobalt(III) complex of bis- N,N ′-disubstituted oxamides catalyses the oxidative decarboxylation of α-hydroxy acids with molecular oxygen/pivalaldehyde with very good yields. This reaction offers an interesting alternative in the use of methyl mandelate as a convenient benzoyl anion equivalent.

Synthetic Application of Homogeneous Charge Transfer Catalysis in the Electrocarboxylation of Benzyl Halides

1998

The results of an investigation on the performances of some outer sphere electron transfer homogeneous catalysts in the electrocarboxylation of 1-(p-isobutyl-phenyl)-1-chloroethane to 2-(p-isobutyl-phenyl)-propionic acid (Ibuprofen), using as catalysts the esters of benzoic and o-, m-, and p-phtalic acids, are reported. The performances of the catalysts are evaluated on the basis of the following parameters: faradic yields of the carboxylation and decomposition of the catalyst. The performances of dimethylisophtalate have been examined in greater detail. The rate of decomposition of the catalyst is related to the molar ratio [halide]/[catalyst].

Three‐Component Castagnoli‐Cushman Reaction of 3‐Arylglutaconic Acid Anhydrides, Carbonyl Compounds, and Ammonium Acetate: a Quick and Flexible Way t…

2021

Photoinduced functionalization of the C-20 methyl group of the nor-diterpene atractyligenin

2001

Abstract Irradiation of the nor-diterpene atractyligenin at λ =254 nm in methanol gave, on one hand, the decarboxylation product, and provided, on the other hand, the transformation of the C-20 angular methyl into a methylene-carbomethoxy group. A photochemical pathway involving formation of C-19/C-20 bond is suggested.

Synthesis of cyanoacetic acid by electrocatalytic carboxylation of chloroacetonitrile at a silver cathode

2008

An unexpected ring carboxylation in the electrocarboxylation of aromatic ketones

2006

The electrocarboxylation of various aromatic ketones, carried out in N-methyl-2-pyrrolidone (NMP) in a diaphragmless cell equipped with a carbon cathode and an aluminium sacrificial anode, yielded, among the products, the target hydroxy acids, the corresponding alcohols and pinacols and, quite surprisingly, detectable amounts of substituted benzoic acids and cycloexene carboxylic acids. These compounds arise from a never reported before electrocarboxylation on the aromatic ring, respectively, for substitution of an aromatic hydrogen and from an addition reaction. For example, the electrocarboxylation of acetophenone gave rise to the substituted benzoic acids in ortho, para and meta position…