63301-31-5Relevant academic research and scientific papers
Greener and regioselective ring opening of epoxides with TMSCN using potassium salts of magnetic carbon nitride
Azizi, Najmedin,Qomi, Mahnaz,Saadat, Mostafa
, p. 1597 - 1602 (2020/10/19)
Abstract: Potassium salts of magnetic graphitic carbon nitride (Fe3O4?g-C3N4-K) synthesized and proved to be a green and recyclable catalyst for rapid and regioselective ring opening of epoxides with TMSCN, yiel
Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles
Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca
supporting information, 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.
Synthesis and characterization of a novel Fe3O4@SiO2/bipyridinium dichloride nanocomposite and its application as a magnetic and recyclable phase-transfer catalyst in the preparation of β-azidoalcohols, β-cyanohydrins, and
Kiasat, Ali Reza,Chadorian, Fatemeh,Saghanezhad, Seyyed Jafar
, p. 1297 - 1306 (2015/12/11)
β-Azidoalcohols, β-cyanohydrins, and β-acetoxy alcohols have been synthesized in the presence of a Fe3O4@SiO2/bipyridinium nanocomposite (Fe3O4@SiO2/BNC) as a novel magnetic and recyclable
Cytochrome P450 catalyzed oxidative hydroxylation of achiral organic compounds with simultaneous creation of two chirality centers in a single C-H activation step
Roiban, Gheorghe-Doru,Agudo, Ruben,Reetz, Manfred T.
supporting information, p. 8659 - 8663 (2014/08/18)
Regio- and stereoselective oxidative hydroxylation of achiral or chiral organic compounds mediated by synthetic reagents, catalysts, or enzymes generally leads to the formation of one new chiral center that appears in the respective enantiomeric or diastereomeric alcohols. By contrast, when subjecting appropriate achiral compounds to this type of C-H activation, the simultaneous creation of two chiral centers with a defined relative and absolute configuration may result, provided that control of the regio-, diastereo-, and enantioselectivity is ensured. The present study demonstrates that such control is possible by using wild type or mutant forms of the monooxygenase cytochrome P450 BM3 as catalysts in the oxidative hydroxylation of methylcyclohexane and seven other monosubstituted cyclohexane derivatives.
Facile synthesis of an organic-inorganic nanocomposite, PEG-silica, by sol-gel method; Its characterization and application as an efficient catalyst in regioselective nucleophilic ring opening of epoxides: Preparation of β-azido alcohols and β-cyanohydrin
Kiasat, Ali Reza,Nazari, Simin,Davarpanah, Jamal
, p. 124 - 130 (2014/03/21)
The sol-gel method was used for the synthesis of a PEG-silica hybrid. In order to introduce PEG into the cavities of silica gel, first, the bis(3-trimethoxysilylpropyl)-polyethylene glycol precursor was synthesized by the reaction of 3-chloropropyltrimeth
Silica-bound 3-{2-[poly(ethylene glycol)]ethyl}-substituted 1-methyl-1H-imidazol-3-ium bromide: A recoverable phase-transfer catalyst for smooth and regioselective conversion of oxiranes to β-hydroxynitriles in water
Reza Kiasat, Ali,Ayashi, Neda,Fallah-Mehrjardi, Mehdi
, p. 275 - 279 (2013/03/28)
A series of β-hydroxynitriles were efficiently synthesized from the regioselective ring opening of oxiranes by cyanide anion in the presence of silica-bound 3-{2-[poly(ethylene glycol)]ethyl}-substituted 1-methyl-1H- imidazol-3-ium bromide (SiO2-PEG-ImBr) as a novel recoverable phase-transfer catalyst in H2O (Scheme 1 and Table 2). The workup procedure was straightforward, and the catalyst could be reused over four times with almost no loss of catalytic activity and selectivity. Copyright
An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation
He, Weimin,Li, Chaoqun,Zhang, Liming
supporting information; experimental part, p. 8482 - 8485 (2011/07/08)
The first efficient intermolecular reaction of gold carbene intermediates generated via gold-catalyzed alkyne oxidation has been realized using nitriles as both the reacting partner and the reaction solvent, offering a generally efficient synthesis of 2,5-disubstituted oxazoles with broad substrate scope. The overall reaction is a [2 + 2 + 1] annulation of a terminal alkyne, a nitrile, and an oxygen atom from an oxidant. The reaction conditions are exceptionally mild, and a range of functional groups are easily tolerated. With complex and/or expensive nitriles, only 3 equiv could be sufficient to achieve serviceable yields in the absence of any solvent and using only 1 mol % BrettPhosAuNTf2 as the catalyst.
An environmentally benign catalytic method for efficient and selective nucleophilic ring opening of oxiranes by zirconium tetrakis(dodecyl Sulfate)
Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Aliabadi, Marzieh
scheme or table, p. 405 - 413 (2010/05/19)
An operationally simple and environmentally benign protocol for a highly regio- and chemoselective preparation of β-substituted alcohols by means of ring-opening reactions of oxiranes with various aliphatic alcohols, H 2O, NaN3 , and NaCN as nucleophiles in the presence of catalytic amounts of zirconium tetrakis(dodecyl sulfate) as Lewis acid/surfactant-combined catalysts (LASCs) was developed. The high efficiency of the catalyst was confirmed by the high product yields obtained within desired times and, in particularly by the reusability of the ZrIV complex.
Ionic acylating agents for the enzymatic resolution of sec-alcohols in ionic liquids
Lourenco, Nuno M. T.,Monteiro, Carlos M.,Afonso, Carlos A. M.
supporting information; experimental part, p. 6938 - 6943 (2011/02/24)
Potential acylating agents containing pendant ionic groups have been screened for the enzymatic kinetic resolution of rac-secondary alcohols in ionic liquids with CAL-B as biocatalyst. This study has allowed the identification of the 1-methyl-3-alkylimidazolium cation attached to a carboxylate group through a C10-alkyl chain as an efficient acylating agent for this transformation. This strategy was applied to the resolution of 2-hydroxycyclohexanecarbonitrile in which the 1R,2S enantiomer was isolated in 35 % ee (73 % yield) and the 1S,2R enantiomer in 97 % ee (23 % yield). Potential acylating agents containing pendant ionic groups have been screened for the enzymatic kinetic resolution of rac-secondary alcohols in ionic liquids with CAL-B as biocatalyst. This study has allowed theidentification of the 1-methyl-3-alkylimidazolium cation attached to a carboxylate group through a C10-alkyl chain as an efficient acylating agent for this transformation. Copyright
LiOH-catalyzed simple ring opening of epoxides under solvent-free conditions
Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad
experimental part, p. 1550 - 1557 (2010/09/06)
LiOH has been found to be a very simple and selective catalyst for the rapid and mild synthesis of β-hydroxy sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions. Copyright Taylor & Francis Group, LLC.
