29559-26-0Relevant academic research and scientific papers
Unanticipated Silyl Transfer in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis Using Silyl Nitronates
Matviitsuk, Anastassia,Greenhalgh, Mark D.,Taylor, James E.,Nguyen, Xuan B.,Cordes, David B.,Slawin, Alexandra M. Z.,Lupton, David W.,Smith, Andrew D.
supporting information, p. 335 - 339 (2020/01/11)
The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of ?3-nitro-substituted silyl esters containing up to two contiguous stereocenters in good yields with excellent enantioselectivities (up to 93% yield and 99:1 er). The serendipitously discovered formation of silyl ester products in this reaction demonstrates a novel platform for catalyst turnover in α,β-unsaturated acyl ammonium catalysis.
Regioselective synthesis of 3,4-diaryl-5-unsubstituted isoxazoles, analogues of natural cytostatic combretastatin A4
Chernysheva, Natalia B.,Maksimenko, Anna S.,Andreyanov, Fedor A.,Kislyi, Victor P.,Strelenko, Yuri A.,Khrustalev, Victor N.,Semenova, Marina N.,Semenov, Victor V.
supporting information, p. 511 - 518 (2018/02/15)
4,5-Diarylisoxazoles are potent antiproliferative tubulin-targeting agents. Their isomeric 3,4-diaryl-5-unsubstituted isoxazoles are hardly accessible. The synthesis of 3,4-diaryl-5-unsubstituted isoxazoles 13 was designed based on a condensation of arylb
Synthesis of 3,4-diaryl-5-carboxy-4,5-dihydroisoxazole 2-oxides as valuable synthons for anticancer molecules
Chernysheva, Natalia B.,Maksimenko, Anna S.,Andreyanov, Fedor A.,Kislyi, Victor P.,Strelenko, Yuri A.,Khrustalev, Victor N.,Semenova, Marina N.,Semenov, Victor V.
, p. 6728 - 6735 (2017/10/25)
The convenient regioselective scalable synthesis of 3,4-diaryl-5-carboxy-4,5-dihydroisoxazole 2-oxides was developed based on a condensation of simple starting materials (arylbenzaldehydes, arylnitromethanes, and ethoxycarbonylmethylpyridinium bromide) un
Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group
Jiang, Minghui,Feng, Lifei,Feng, Juanjuan,Jiao, Peng
supporting information, p. 2210 - 2213 (2017/05/12)
1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an α-aryl group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey’s oxazaborolidine catalyst. Specifically, the TIPS nitronate with an α-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.
2-Aryl-2-nitroacetates as central precursors to aryl nitromethanes, α-ketoesters, and α-amino acids
Metz, Alison E.,Kozlowski, Marisa C.
, p. 717 - 722 (2013/02/25)
Nitroarylacetates are useful small molecular building blocks that act as precursors to α-ketoesters and aryl nitromethanes as well as α-amino acids. Methods were developed that produce each of these compound types in good yields. Two different conditions
Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides
Walvoord, Ryan R.,Kozlowski, Marisa C.
, p. 8859 - 8864 (2013/09/24)
A method for the formation of arylnitromethanes is described that employs readily available aryl halides or triflates and small amounts of nitromethane in a dioxane solvent, thereby reducing the hazards associated with this reagent. Specifically, 2-10 equiv (1-5% v/v) of nitromethane can be employed in comparison to prior work that used nitromethane as solvent (185 equiv). The present transformation provides high yields at relatively low temperatures and tolerates an array of functionality, including heterocycles and substantial steric encumbrance.
Palladium-catalyzed nitromethylation of aryl halides: An orthogonal formylation equivalent
Walvoord, Ryan R.,Berritt, Simon,Kozlowski, Marisa C.
supporting information; experimental part, p. 4086 - 4089 (2012/09/22)
An efficient cross-coupling reaction of aryl halides and nitromethane was developed with the use of parallel microscale experimentation. The arylnitromethane products are precursors for numerous useful synthetic products. An efficient method for their direct conversion to the corresponding oximes and aldehydes in a one-pot operation has been discovered. The process exploits inexpensive nitromethane as a carbonyl equivalent, providing a mild and convenient formylation method that is compatible with many functional groups.
Kinetic study of proton-transfer reactions of phenylnitromethanes. Implication for the origin of nitroalkane anomaly
Ando, Kenichi,Shimazu, Yu,Seki, Natsuko,Yamataka, Hiroshi
experimental part, p. 3937 - 3945 (2011/07/08)
Measurements of rate constants and substituent effects for three important elementary steps of proton-transfer reactions of phenylnitromethane were reported. The Hammett ? values for the deprotonation of ArCH2NO 2 with OH-
The synthesis of phenolic propane-1, 2- and 1,3-diols as intermediates in immobilised chelatants for the borate anion
Tyman, John H. P.,Payne
, p. 691 - 695 (2007/10/03)
The isomeric 3-(hydroxyphenyl)propane-1, 2-diols have been synthesised from allylic precursors by epoxidation and cleavage. Several different methods have been examined for obtaining 1-(methoxyphenyl)propane-1, 3-diols. 2-(methoxyphenyl)propane-1, 3-diols and certain hydroxy analogues have been obtained from benzaldoximes converted by oxidation to methoxy- and benzyloxynitromethylbenzenes followed by hydroxymethylation with formaldehyde and catalytic hydrogenation.
Methyltrioxorhenium-catalyzed oxidation of aromatic aldoximes
Cardona, Francesca,Soldaini, Gianluca,Goti, Andrea
, p. 1553 - 1556 (2007/10/03)
The first catalytic oxidation of aryl oximes to nitro compounds by means of methyltrioxorhenium and urea hydroperoxide is reported. The formation of carbamates, probably occurring through formation of nitrile oxide intermediates, has been observed from 2,6-disubstituted aryl oximes.
