121617-17-2Relevant academic research and scientific papers
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 (2003)
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.
Ring opening of 3-bromo-2-isoxazolines to β-hydroxy nitriles
Kociolek, Martin G.,Kalbarczyk, Kyle P.
, p. 4387 - 4394 (2004)
3-Bromo-2-isoxazolines were converted to the corresponding β-hydroxy nitriles by treatment with sodium iodide in the presence of either chlorotrimethylsilane or para-toluenesulfonic acid. Both methods gave β-hydroxy nitriles under relatively mild conditio
Reformatsky reactions with SmI2 in catalytic amount
Orsini, Fulvia,Lucci, Elvira Maria
, p. 1909 - 1911 (2005)
A substoichiometric protocol for Reformatsky-type addition of α-haloesters, α-haloketones, α-halonitriles, and α-halophosphonates to carbonyl compounds has been developed. β-Hydroxyesters and β-hydroxynitriles were obtained in good to excellent yields.
Connecting Neutral and Cationic Pathways in Nickel-Catalyzed Insertion of Benzaldehyde into a C-H Bond of Acetonitrile
Smith, Jacob B.,Miller, Alexander J. M.
, p. 4669 - 4677 (2015)
Nickel catalysts supported by diethylamine- or aza-crown ether-containing aminophosphinite (NCOP) pincer ligands catalyze the insertion of benzaldehyde into a C-H bond of acetonitrile. The catalytic activity of neutral (NCOP)Ni(OtBu) and cation
One step conversion of highly dipolarophilic olefins to α-hydroxy-β-cyanoadducts with metal fulminate
You, Zhengqing,Lee, Henry Joung
, p. 1165 - 1168 (1996)
Olefins conjugated with carbonyl, carboxylic ester, and phenyl groups as well as highly strained non-conjugated olefin norbornylene were converted to their corresponding α-hydroxy-β-cyanoadducts by treatment with mercuric fulminate and lithium bromide. Th
Synthesis of β-hydroxy nitriles and 1,3-amino alcohols from epoxides using acetone cyanohydrin as a LiCN precursor
Ciaccio, James A.,Smrtka, Michael,Maio, William A.,Rucando, David
, p. 7201 - 7204 (2004)
The reaction of acetone cyanohydrin with MeLi affords a LiCNA·acetone complex that can be made to react with epoxides in THF, either in one-pot or using isolated samples of the cyanide complex, to cleanly afford β-hydroxy nitriles upon aqueous workup; in situ hydride reduction of nitriles affords 1,3-amino alcohols.
ACTIVATION DE LA LIAISON C-H FAIBLEMENT ACIDE PAR ADSORPTION SUR KF-Al2O3
Villemin, Didier,Ricard, Michele
, p. 1059 - 1060 (1984)
Condesation of poorly acidic carbon compounds (pka 18-30) with benzaldehyde was achieved by adsorption without solvent on KF-Al2O3.KF-Al2O3 appears as a stronger base than KF.
Steric vs. electronic effects in the Lactobacillus brevis ADH-catalyzed bioreduction of ketones
Rodriguez, Cristina,Borzecka, Wioleta,Sattler, Johann H.,Kroutil, Wolfgang,Lavandera, Ivan,Gotor, Vicente
, p. 673 - 681 (2014)
Lactobacillus brevis ADH (LBADH) is an alcohol dehydrogenase that is commonly employed to reduce alkyl or aryl ketones usually bearing a methyl, an ethyl or a chloromethyl as a small ketone substituent to the corresponding (R)-alcohols. Herein we have tested a series of 24 acetophenone derivatives differing in their size and electronic properties for their reduction employing LBADH. After plotting the relative activity against the measured substrate volumes we observed that apart from the substrate size other effects must be responsible for the activity obtained. Compared to acetophenone (100% relative activity), other small substrates such as propiophenone, α,α, α-trifluoroacetophenone, α-hydroxyacetophenone, and benzoylacetonitrile had relative activities lower than 30%, while medium-sized ketones such as α-bromo-, α,α-dichloro-, and α,α-dibromoacetophenone presented relative activities between 70% and 550%. Moreover, the comparison between the enzymatic activity and the obtained final conversions using an excess or just 2.5 equiv. of the hydrogen donor 2-propanol, denoted again deviations between them. These data supported that these hydrogen transfer (HT) transformations are mainly thermodynamically controlled. For instance, bulky α-halogenated derivatives could be quantitatively reduced by LBADH even employing 2.5 equiv. of 2-propanol independently of their kinetic values. Finally, we found good correlations between the IR absorption band of the carbonyl groups and the degrees of conversion obtained in these HT processes, making this simple method a convenient tool to predict the success of these transformations. The Royal Society of Chemistry.
Highly regioselective conversion of epoxides to β-hydroxy nitriles using metal(II) Schiff base complexes as new catalysts under mild conditions
Naeimi, Hossein,Karshenas, Azam
, p. 234 - 238 (2013)
Epoxides undergo efficient ring opening with potassium cyanide in acetonitrile in the presence of metal Schiff base complexes as catalysts. This method was carried out under neutral and mild conditions with both high yields and high regioselectivity within a short period of time. Thus, several β-hydroxy nitriles, useful intermediates for the synthesis of biologically active molecules, were easily obtained at room temperature.
Practical oxirane ring opening with in situ prepared LiCN; synthesis of (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-1 -butanenitrile
Tsuruoka, Akihiko,Negi, Shigeto,Yanagisawa, Manabu,Nara, Kazumasa,Naito, Toshihiko,Minami, Norio
, p. 3547 - 3557 (1997)
Trisubstituted oxirane 1 was regiospecifically opened with LiCN in situ prepared from acetone cyanohydrin and LiH to provide the corresponding β-hydroxy nitrile 2 in satisfactory yield, enabling us to manufacture a key intermediate for a new antifungal agent on a multi-kg scale. Some applications of this method to the ring opening of other oxiranes and nucleophilic substitution are also described.
