1403500-15-1Relevant 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
, p. 4339 - 4346 (2012)
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
Preparation of sugar-derived 1,2-diamines via indium-catalyzed aza-Henry-type reaction: Application to the synthesis of 6-amino-1,6- dideoxynojirimycin
Soengas, Raquel G.,Silva, Artur M.S.
, p. 2156 - 2159 (2013/05/08)
The combination of (p-methoxyphenyl)imine, a bromonitroalkane, and zinc in the presence of catalytic indium allows straightforward access to β-nitroamine derivatives. The use of chiral sugar-derived imines furnished the corresponding β-nitroamines in high yields and stereoselectivities, from which the corresponding 1,2-diamines were easily obtained. The synthetic utility of the sugar-derived 1,2-diamines in the preparation of iminosugars was illustrated in a concise synthesis of 6-amino-1,6-dideoxynojirimycin.
