149495-00-1Relevant academic research and scientific papers
Heterogeneous chiral copper complexes of amino alcohol for asymmetric nitroaldol reaction
Mayani, Vishal J.,Abdi, Sayed H. R.,Kureshy, Rukhsana I.,Khan, Noor-Ul H.,Das, Anjan,Bajaj, Hari C.
, p. 6191 - 6195 (2010)
Figure presented. Chiral amino alcohols supported on mesoporous silicas were synthesized and evaluated as a new class of chiral ligands in copper-catalyzed nitroaldol reaction under heterogeneous and mild reaction conditions. The activity and enantioselec
C2 symmetric copper (II) complexes of L-valine and L-phenyl alanine based chiral diimines for catalytic asymmetric Henry reaction
Ananthi, Nallamuthu,Johnson, S. Jesu,Kumar, K. Vinoth,Nixon, Peter Daniel
, (2021)
New C2 symmetric chiral diimines were synthesized from the amino acids L-valine and L-phenyl alanine. In situ copper (II) complexes of the chiral diimine ligands were found to catalyze asymmetric Henry reaction. The chiral nitro aldols were formed in excellent yield (99%) and ee (99%). The synthetic utility of the chiral catalysts were screened with various substituted prochiral aromatic and heteroaromatic aldehydes. Possible catalytic cycle for the chiral diimine copper complex catalyzed asymmetric Henry reaction has been proposed. The stereoselectivity of the asymmetric Henry reaction was discussed based on the transition state in the catalytic cycle.
Facile construction of functionalized periodic mesoporous organosilica for Ir-catalyzed enantioselective reduction of α-cyanoacetophenones and α-nitroacetophenones
Chen, Chen,Kong, Lingyu,Cheng, Tanyu,Jin, Ronghua,Liu, Guohua
, p. 10891 - 10893 (2014)
A facile method to construct chiral organoiridium-functionalized periodic mesoporous organosilica is developed. The heterogeneous catalyst displays excellent catalytic efficiency in the enantioselective reduction of α-cyanoacetophenones and α-nitroacetoph
A biocatalytic Henry reaction - The hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions
Purkarthofer, Thomas,Gruber, Karl,Gruber-Khadjawi, Mandana,Waich, Kerstin,Skranc, Wolfgang,Mink, Daniel,Griengl, Herfried
, p. 3454 - 3456 (2006)
(Figure Presented) Novel enzyme activity: Biocatalytic Henry reactions with nitromethane and nitroethane yielded the corresponding nitroalcohols with good enantio- and diastereo-control in the presence of the hydroxynitrile lyase from the tropical rubber tree Hevea brasiliensis. Molecular modeling and deuterated starting materials were used in mechanistic investigations.
Copper complexes bearing methylthiophenyl and methylfuranyl derivatives of (R,R)-1,2-diaminocyclohexane: X-ray structures and catalytic exploitation in Henry reaction
Cho, Jaewon,Lee, Gang Ho,Nayab, Saira,Jeong, Jong Hwa
, p. 198 - 203 (2015)
Abstract Two novel dichloro Cu(II) complexes of (R,R)-N1,N2-bis((5-methylthiophen-2-yl)methyl)cyclohexane-1,2-diamine (MTCHD) and (R,R)-N1,N2-bis((5-methylfuran-2-yl)methyl)cyclohexane-1,2-diamine (MFCHD) ligand
Evaluation of 5-cis-Substituted Prolinamines as Ligands in Enantioselective, Copper-Catalyzed Henry Reactions
Kaldun, Johannes,Prause, Felix,Scharnagel, Dagmar,Freitag, Frederik,Breuning, Matthias
, p. 1846 - 1856 (2016)
The development of a new catalytic system for enantioselective Henry reactions, which permits superb 99 % ee with a broad variety of aldehydes, is presented. In-depth structure-selectivity investigations with 33 5-cis-substituted prolinamines, prepared fr
Revisit to Henry reaction by non conventional heterogeneous and efficient catalyst for nitroalcohol synthesis
Jadhav, Swati D.,Patil, Rupesh C.,Jagdale, Ashutosh A.,Patil, Suresh S.
, p. 593 - 606 (2021/11/03)
A sustainable, green and efficient process for the synthesis of 2-nitro alcohol derivatives from different substituted aromatic aldehydes with nitroalkane by stirring at ambient temperature with high product yield is reported. Adoption of very mild reaction conditions, use of Calcined Eggshell (CES) as natural catalyst and simple workup are expected to contribute to the development of environmentally benign synthetic method for Henry (nitroaldol) reaction. CES is ecologically safe, inexpensive, and attractive heterogeneous base catalyst obtained from renewable resources, thus opening a new perspective for this process. Graphical abstract: [Figure not available: see fulltext.]
Polymeric nanoassembly of imine functionalized magnetite for loading copper salts to catalyze Henry and A3-coupling reactions
Rathod, Prakash B.,Kumar, K.S. Ajish,Athawale, Anjali A.,Pandey, Ashok K.
, (2021/03/09)
Poly(ethylenimine) was grafted on the magnetite (Fe3O4) nanoparticles, and subsequently reacted with different aldehydes to form the imine functionalities (Fe3O4-Imine NPs). Thus formed Fe3O4/su
(3S,4S)-N-substituted-3,4-dihydroxypyrrolidines as ligands for the enantioselective Henry reaction
Rénio, Márcia R.R.,Sousa, Francisco J.P.M.,Tavares, Nélia C.T.,Valente, Artur J.M.,da Silva Serra, M. Elisa,Murtinho, Dina
, (2021/02/03)
The enantioselective Henry reaction is a very important and useful carbon–carbon bond forming reaction. The execution of this reaction requires the use of efficient chiral catalysts. In this work, in situ formed complexes of N-substituted dihydroxypyrrolidines, chiral ligands derived from L-tartaric acid and amines, were evaluated as catalysts in the enantioselective Henry reaction. The results showed that the nature of the N-substituent on the ligand significantly influences the outcome of the reaction. Best results were obtained using a Cu (II) complex of (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine, in the presence of DIPEA, for the reaction of aromatic aldehydes with nitromethane, at room temperature, originating products with er up to 92:8 (R:S) and conversions up to 96%. The interaction between the pyrrolidine ligand and the copper ion, in isopropanol, was followed by UV-vis spectrophotometry, showing a 1:1 stoichiometry and a binding constant of 4.4. The results obtained will contribute to the design and development of more efficient chiral catalysts for this type of reaction.
Nitration of Alkenes and Oxiranes with Nitrogen(IV) Oxide in Liquid and Supercritical Carbon Dioxide Media
Ivanov, R. E.,Zharkov, M. N.,Zlotin, S. G.
, p. 209 - 212 (2022/02/22)
Abstract: For the first time the reactions of radical nitration of alkenes and oxiranes with nitrogen dioxide in the liquid and supercritical carbon dioxide (sc-CO2) media were carried out. Using octene-1, styrene, and their derivatives as exam
