2236-11-5Relevant academic research and scientific papers
A heterogenized cobaltate catalyst on a bis-imidazolium-based covalent triazine framework for hydroesterification of epoxides
Rajendiran, Senkuttuvan,Gunasekar, Gunniya Hariyanandam,Yoon, Sungho
supporting information, p. 12256 - 12262 (2018/07/24)
An imidazolium-cobaltate-based heterogeneous catalyst exhibits advantages over its homogeneous counterpart in the synthesis of β-hydroxyesters from epoxides. However, leaching of cobaltate from the catalytic support decreases the selectivity and recyclability of the catalyst. To overcome such drawbacks, a bis-imidazolium-based covalent triazine framework (CTF) is employed as a catalytic support for the hydroesterification catalyst to reduce cobaltate leaching by the intramolecular anion stabilization effect of the multi-imidazolium moiety, resulting in an excellent selectivity for the β-hydroxyester and unprecedented recyclability.
Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles
Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca
, p. 3366 - 3369 (2016/07/26)
A stereoselective bioreduction of 2-oxocycloalkanecarbonitriles was concurrently coupled to a whole cell-catalyzed nitrile hydrolysis in one-pot. The first step, mediated by ketoreductases, involved a dynamic reductive kinetic resolution, which led to 2-hydroxycycloalkanenitriles in very high enantio- and diastereomeric ratios. Then, the simultaneous exposure to nitrile hydratase and amidase from whole cells of Rhodococcus rhodochrous provided the corresponding 2-hydroxycycloalkanecarboxylic acids with excellent overall yield and optical purity for the all-enzymatic cascade.
Non-Cp titanium alkoxide-based homolytic ring-opening of epoxides by an intramolecular hydrogen abstraction in β-titanoxy radical intermediates
Kawaji, Tsuyoshi,Shohji, Noriaki,Miyashita, Kenji,Okamoto, Sentaro
supporting information; experimental part, p. 7857 - 7859 (2011/09/15)
A low-valent titanium species derived in situ from Ti(O-i-Pr)4, Me3SiCl and Mg powder in tetrahydrofuran reacted with epoxides to selectively provide less hindered alcohols via a homolytic ring-opening of epoxides, in which the intermediate β-titanoxy radical intramolecularly abstracted a hydrogen atom from an alkoxy moiety in the titanium complexes.
Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions
Maegawa, Tomohiro,Akashi, Akira,Yaguchi, Kiichiro,Iwasaki, Yohei,Shigetsura, Masahiro,Monguchi, Yasunari,Sajiki, Hironao
experimental part, p. 6953 - 6963 (2010/02/28)
An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H 2 pressures (10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are hydrogenated to the corresponding cyclohexyl and heterocyclic compounds in good to excellet yields. The use of Ru/C, less expensive than Rh/C, affords an effective and practical method for the hydrogenation of arenes including phenols. Both catalysts can be reused several times after simple filtration without any significant loss of catalytic activity.
Hexafluoroisopropanol: A powerful solvent for the hydrogenation of functionalized aromatic compounds
Fache, Fabienne,Piva, Olivier
, p. 1294 - 1296 (2007/10/03)
Various substituted aromatic compounds have been reduced under H 2 using RuCl3. The fluorous solvent hexafluoroisopropanol turned out to be particularly efficient in the case of compounds difficult to reduce in organic solvents.
Preparation of β-hydroxyesters from isoxazolines. A selective Ni 0bpy-catalyzed electrochemical method
Caetano, Viviane F.,Demnitz, F.W. Joachim,Diniz, Flamarion B.,Mariz Jr., Ronaldo M.,Navarro, Marcelo
, p. 8217 - 8220 (2007/10/03)
An electrocatalytic method for the reductive N-O cleavage of isoxazolines is described. Ni0bpy, generated in situ, was used to promote selective ring opening of 3-methoxy-5-phenylisoxazoline (1a) and 3-methoxy-[4,5]cyclohexylisoxazoline (1b). DMF and NaI were used as solvent and supporting electrolyte, and β-hydroxyesters 2a and 2b were obtained in high yields respectively, after acid hydrolysis. β-Hydroxynitriles 3a and 3b were also identified as side products.
Efficient cyclization of ω-oxo-α,β-unsaturated esters using lithium thiolate-initiated Michael-aldol tandem reaction
Ono, Masashi,Nishimura, Katsumi,Nagaoka, Yasuo,Tomioka, Kiyoshi
, p. 6979 - 6982 (2007/10/03)
The reaction of ω-oxo-α,β-unsaturated esters with lithium thiolates afforded the Michael-aldol tandem cyclization products in good to perfect stereoselectivity depending on the nature of thiolates.
CONVERSION OF ISOXAZOLINES TO β-HYDROXY ESTERS. SYNTHESIS OF 2-DEOXY-D-RIBOSE
Caldilora, P.,Ciancaglione, M.,De Amici, M.,De Micheli, C.
, p. 4647 - 4650 (2007/10/02)
A simple and efficient preparation of β-hydroxy esters with a well-defined stereochemistry has been developed using 3-bromoisoxazolines as key-intermediates.A synthesis of 2-deoxy-D-ribose is also reported.
Phosphorylated Sugars. Part 23. Synthesis and Reactions of Phosphodiesters containing 2-Aminoethanol and a Polyfunctional Alcohol and their Behaviour during Acid- and Base-catalysed Hydrolysis
Trigalo, Francois,Szabo, Ladislas
, p. 1733 - 1744 (2007/10/02)
Phosphodiesters of 2-aminoethanol and of polyhydroxylated alcohols and sugars have been synthesised; their behaviour in M-HCl and in saturated (ca. 0.2 M) Ba(OH)2 solutions at 100 deg C have been examined.With the exception of 2-aminoethyl ethyl phosphate which, in acidic medium, yielded 2-aminoethylphosphate, free 2-aminoethanol and phosphorylated polyols or sugars were the main products formed.Because of simultaneously and/or sequentially occurring reactions the structures of the phosphorylated derivatives formed gave no unambiguous information regarding the structure of the initial phosphodiester.
