21101-82-6Relevant academic research and scientific papers
Palladium mediated chemoselective reduction of α,β-unsaturated cyano esters with potassium formate
Basu, Basudeb,Bhuiyan, Md. Mosharef Hossain,Jha, Satadru
, p. 291 - 296 (2003)
A number of α,Β-unsaturated cyano esters have been chemoselectively reduced with potassium formate as hydrogen donor, and palladium(II) acetate as homogeneous catalyst, in DMF without any concomitant reduction of cyano or carboxylate or halogen groups.
Tandem catalytic condensation and hydrogenation processes in ionic liquids
Baidossi, Mubeen,Joshi, Asutosh V.,Mukhopadhyay, Sudip,Sasson, Yoel
, p. 1885 - 1887 (2005)
A domino reaction composed of a Knoevenagel condensation combined with a simultaneous catalytic hydrogenation is reported in an ionic liquid solvent under mild conditions (298-363 K and 300 kPa). No interference between the catalysts (Pd/C and amine acetate salt) of the two diverse steps was monitored. The product could be neatly extracted by diethyl ether and the solvent containing the catalysts could be recycled and reused five times without any loss in activity or selectivity. The same methodology in a common organic solvent such as DMA resulted in significant competing parallel hydrogenation of the aldehyde to alcohol.
Metalated nitriles: Internal 1,2-asymmetric induction
Fleming, Fraser F.,Liu, Wang,Ghosh, Somraj,Steward, Omar W.
, p. 2803 - 2810 (2008/09/19)
(Chemical Equation Presented) Alkylations of conformationally constrained acyclic nitriles containing vicinal dimethyl groups and an adjacent phenyl group or trisubstituted alkene are exceptionally diastereoselective. Probing the alkylation stereoselectivity with a series of C- and N-metalated nitriles implicates a reactive conformation in which an sp2-hybridized substituent projects over the metalated nitrile to avoid allylic strain. Steric screening thereby directs the electrophilic attack to the face of the metalated nitrile opposite the projecting substituent. Excellent stereoselectively is maintained in a diverse range of alkylations that efficiently install quaternary centers, even with isopropyliodide in which a contiguous array of tertiary-quaternary-tertiary stereocenters is created! Screening the conformational requirements with a series of acyclic nitriles and esters reveals the key structural requirements for high selectivity while providing a robust, predictive model that accounts for comparable ester alkylations affording the opposite diastereomer! The intensive survey of metalated nitrile alkylations identifies the key structural features required for high 1,2-asymmetric induction, addresses the long-standing challenge of asymmetric alkylations with acylic metalated nitriles, and provides a versatile method for installing hindered quaternary centers with excellent stereocontrol.
Co-immobilized formate anion and palladium on a polymer surface: A novel heterogeneous combination for transfer hydrogenation
Basu, Basudeb,Das, Sajal,Das, Pralay,Nanda, Ashish K.
, p. 8591 - 8593 (2007/10/03)
A novel heterogeneous combination of a formate reagent and palladium catalyst co-immobilized on a resin support has been developed and shown to be highly efficient and recyclable for transfer hydrogenation of alkenes, imines, nitroarenes and 1,2-dicarbonyl compounds.
Reduction of activated conjugated alkenes by the InCl3-NaBH 4 reagent system
Ranu, Brindaban C.,Samanta, Sampak
, p. 7901 - 7906 (2007/10/03)
A combination of a catalytic amount of indium (III) chloride and sodium borohydride in acetonitrile reduces selectively the carbon-carbon double bonds in conjugated alkenes such as α,α-dicyano olefins, α,β-unsaturated nitriles, cyanoesters, cyanophosphonate and dicarboxylic esters. However, reduction of chalcones is little different. They are reduced to a mixture of saturated ketones and alcohols if the reaction mixture is quenched with H2O, whereas quenching with MeOH leads to saturated alcohols only.
Use of indium hydride (Cl2InH) for chemoselective reduction of the carbon-carbon double bond in conjugated alkenes
Ranu, Brindaban C.,Samanta, Sampak
, p. 7405 - 7407 (2007/10/03)
Indium hydride (Cl2InH) generated in situ from a combination of a catalytic amount of indium(III) chloride and sodium borohydride selectively reduces the carbon-carbon double bond in conjugated alkenes such as α,α-dicyano olefins, α,β-unsaturated nitriles, cyano esters, cyanophosphonate, diesters and ketones.
Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents
Araki, Shuki,Horie, Tomoaki,Kato, Motoshi,Hirashita, Tsunehisa,Yamamura, Hatsuo,Kawai, Masao
, p. 2331 - 2334 (2007/10/03)
Triorganogallium and -indium reagents reacted with α,β-unsaturated nitrile and carbonyl compounds to give 1,4-addition products regioselectively. The reaction of allylgallium and allylindium sesquihalides with α,β-unsaturated carbonyl compounds proceeded
Concave reagents, 30. Diastereoselective generation of quaternary stereocenters by ligand-controlled palladium-catalyzed allylations
Meynhardt,Lüning,Wolff,N?ther
, p. 2327 - 2335 (2007/10/03)
The 1,2-asymmetric induction in the formation of new quaternary centers by palladium-catalyzed allylation of substituted cyanoacetates 1a-c was controlled by using 2,9-disubstituted 1,10-phenanthrolines as ligands, giving the allylated products 3a-c with
A convenient new procedure for the construction of highly substituted acetates. Reductive alkylation of α-cyano esters
Shia, Kak-Shan,Chang, Nien-Yin,Yip, Judy,Liu, Hsing-Jang
, p. 7713 - 7716 (2007/10/03)
A convenient, highly efficient general method for the preparation of highly substituted acetates has been developed, making use of reductive alkylation of α-cyano esters as a key operation.
