1403500-09-3Relevant articles and documents
Indium-mediated aza-Henry reaction of imines: Access to 2-nitroamines
Soengas, Raquel G.,Silva, Sandrina,Estevez, Amalia M.,Estevez, Juan C.,Estevez, Ramon J.,Rodriguez-Solla, Humberto
experimental part, p. 4339 - 4346 (2012/10/08)
A new method has been developed to obtain 2-nitroamines by an indium-promoted reaction of bromonitromethane with a variety of imines. On the strength of these results, the reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroamines. Moreover, the indium-mediated reaction of 1-bromo-1-nitroethane and imines afforded 1-methyl-2-nitroamines with remarkably high anti selectivity. The use of chiral sugar-derived imines furnished the corresponding 2-nitroamines with excellent stereoselectivity. A new method to obtain 2-amines by reaction of bromonitromethane with a variety of imines, 2-bromo-2-nitropropanes and chiral sugar-derived aldehydes, promoted by indium is reported. This is the first example of the preparation of 2,2-dialkyl-2-nitroamines by addition to imines. The sugar-derived aldehydes furnished the corresponding 2-nitroamines with excellent stereoselectivity. Copyright