145920-96-3Relevant articles and documents
1,1′-Methylene-bis(1,1′,2,2′,3,3′,4, 4′-octahydroisoquinoline): Synthesis, reaction, resolution, and application in catalytic enantioselective transformations
Yao, Qiong Ji,Judeh, Zaher M.A.
, p. 4086 - 4092 (2011)
The preparation of new chiral 1,3-diamine ligand systems based on the 1,1′-methylene-bis(1,1′,2,2′,3,3′,4,4′- octahydroisoquinoline) framework is described. Synthesis of various mono-, di-, and bridged N-alkyl derivatives are presented. Resolution of one
Enantioselective nitroaldol reaction catalyzed by chiral C 1-tetrahydro-1,1′-bisisoquinoline-copper(I) complexes
Qiong Ji, Yao,Qi, Gao,Judeh, Zaher M.A.
, p. 929 - 935 (2011)
An efficient catalytic system comprising of chiral C1- tetrahydro-1,1′-bisisoquinoline and CuCl in the ratio of 2:1 has been developed for the enantioselective Henry reaction. The catalytic efficiencies of the chiral C1-tetrahydro-1,
Development of new chiral phosphine-salen type ligands and their application in the Cu(I)-catalyzed enantioselective Henry reaction
Jiang, Jia-Jun,Shi, Min
, p. 1376 - 1382 (2007)
Chiral phosphine-salen type ligand L4 prepared from (R)-2-(diphenylphosphino)-1,1′-binaphthyl-2′-amine was found to be a fairly effective chiral ligand for Cu(I)-promoted enantioselective Henry reactions of arylaldehydes with nitromethane to give the corr
Combining fluorous and triazole moieties for the tagging of chiral azabis(oxazoline) ligands
Rasappan, Ramesh,Olbrich, Tobias,Reiser, Oliver
, p. 1961 - 1967 (2009)
New fluorous-tagged azabis(oxazoline) ligands were prepared using the copper-catalyzed azide-alkyne cycloaddition as ligation method. The resulting ligands were tested in copper-catalyzed asymmetric benzoylations (up to 99% ee), nitroaldol (up to 90% ee), and Michael reactions (up to 82% ee). The combination of unpolar fluorinated alkyl chains and polar triazole moieties imposes properties that are beneficial for the catalysts with respect to recyclability and selectivity. The scope and limitation of this strategy in comparison to analogous catalysts immobilized on methoxypolyethylene glycol (MeOPEG) or polystyrene is discussed. Moreover, this study shows that the choice of solvent for a given reaction is crucial to arrive at highly recyclable bis(oxazoline) catalysts.
Novel chiral N4S2- and N6S 3-donor macrocyclic ligands: Synthesis, protonation constants, metal-ion binding and asymmetric catalysis in the henry reaction
Gao, Jian,Martell
, p. 2801 - 2806 (2003)
New Hydrophobic chiral macrocyclic ligands L1-L3 with chiral diamino and thiophene moieties have been synthesized by the Schiff base condensation approach. Protonation constants of L1 and L2 were determined by potentiometry titration. Metal-ion binding experiments exhibited that L1 and L3 are pronounced in selective recognition, Ag+, Cu2+ and Ca 2+ ions among the surveyed metal ions (Cu2+, Co 2+, Ni2+, Zn2+, Cd2+, Pb 2+, Ag+, Li+, Na+, K+, and Ca2+). LI was found to spectroscopically detect the presence of Cu2+ and Ca2+ to function as a multiple readout sensor. The detection limit for Ca2+ ions was found to be 9.8 × 10 -5 M in CH2Cl2-MeOH solution. The trimeric chiral ligand L3 has been shown to be an efficient auxiliary in a Zn(II)-mediated enantioselective Henry reaction.
Synthesis of a novel unsymmetrical bisoxazoline ligand with sp2 bridging carbon
Yuryev, Ruslan,Liese, Andreas
, p. 2589 - 2592 (2009)
A novel unsymmetrical bisoxazoline ligand was synthesized in one step by the Knoevenagel condensation of aldehydes with a C2-symmetric indane-derived bisoxazoline having two acidic hydrogens connected to the bridging carbon. The electronic properties of i
Nanocrystalline MgO catalysts for the Henry reaction of benzaldehyde and nitromethane
Xi, Yuanzhou,Davis, Robert J.
, p. 22 - 27 (2011)
Nanocrystalline MgO particles of about 3 nm were examined as catalysts for the Henry reaction between benzaldehyde and nitromethane at 273 K. The surface area of nanocrystalline MgO was greater than 600 m2 g-1 except after thermal tr
One-Pot Enzyme Cascade Catalyzed Asymmetrization of Primary Alcohols: Synthesis of Enantiocomplementary Chiral β-Nitroalcohols
Chatterjee, Ayon,Kumar Padhi, Santosh,Rao, D. H. Sreenivasa
, p. 5310 - 5318 (2021/10/02)
Biocatalytic asymmetrization of inexpensive and stable primary alcohols to prepare enantioenriched β-nitroalcohols is an important development in green chemistry for the production of chiral pharmaceutical intermediates. Herein, we report a one-pot, two-step cascade reaction sequence in which first benzylic alcohols were oxidized to produce corresponding benzaldehydes using horse liver alcohol dehydrogenase (HLADH). The in situ generated aldehydes were then reacted in a biphasic medium with nitromethane by Arabidopsis thaliana hydroxynitrile lyase (AtHNL) or Baliospermum montanum HNL (BmHNL) catalyzed Henry reaction to produce stereoselective β-nitroalcohols with (R) or (S) configuration, respectively. Using HLADH-AtHNL, (R)-β-nitroalcohols were obtained in up to 64% conversion, and HLADH-BmHNL, (S)-β-nitroalcohols in up to 70% conversion, while in both cases excellent stereoselectivity (up to >99% ee) was achieved. The concept was proven by functionalization of sp3 C?H bond of ten simple achiral benzylic alcohols to enantiocomplementary chiral β-nitroalcohols. (Figure presented.).
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
