21080-10-4Relevant articles and documents
Water-compatible hydrogen-bond activation: A scalable and organocatalytic model for the stereoselective multicomponent aza-henry reaction
Cruz-Acosta, Fabio,De Armas, Pedro,Garcia-Tellado, Fernando
, p. 16550 - 16554 (2013)
A study was conducted to demonstrate that H-bond based asymmetric organocatalysis can be performed under the so-called in the presence of water conditions. Nitroalkane, catalyst, dimethylcyclohexylamine, benzaldehyde and aniline were mixed to a 0°C cooled and vigorously stirred aqueous solution of NaOAc/AcOH saturated with NaCl. The organic residues were taken into dichloromethane and decanted off. The combined organic fractions were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel) using a mixture of hexanes/ethyl acetate. From a synthetic point of view, the reaction furnishes enantioenriched b-nitroamines decorated with aromatic or aliphatic substituents at the amine center and a different set of alkyl chains or rings attached to the carbon bearing the nitro functionality. Importantly, the reaction can be scaled up without losing yield and stereoselectivity and with full recovery of the catalyst.
Study on the influence of a sustainable medium for the design of multistep processes: Three-component synthesis of 2-Nitroamines
Piscopo, Calogero G.,Sartori, Giovanni,Mayoral, José A.,Lanari, Daniela,Vaccaro, Luigi,Maggi, Raimondo
, p. 2596 - 2600 (2013/12/04)
An environmentally benign method was developed for the three-component, one-pot synthesis of 2-nitroamines by heating a solution of an aldehyde, an aromatic amine, and a nitroalkane in 20% water–methanol at 60 °C for five hours in the absence of a catalys
