53178-83-9Relevant academic research and scientific papers
Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group
Jiang, Minghui,Feng, Lifei,Feng, Juanjuan,Jiao, Peng
, p. 2210 - 2213 (2017)
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.
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.
