Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: improved reaction conditions and expanded substrate scope.
The copper(II) carboxylate promoted diamination reaction has been improved by the use of the organic soluble copper(II) neodecanoate [Cu(ND)2]. Cu(ND)2 allowed the less-polar solvent dichloroethane (DCE) to be used, and as a consequence, decomposition of less-reactive substrates could be avoided. High diastereoselectivity was observed in the synthesis of 2,5-disubstituted pyrrolidines. Ureas, bis(anilines), and alpha-amido pyrroles derived from 2-allylaniline could also participate in the diamination reaction.
Zabawa
Thomas P
TP
Department of Chemistry, The University at Buffalo, The State University of New York, Buffalo, NY 14260, USA.
Chemler
Sherry R
SR
D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D008024:Ligands; D015394:Molecular Structure; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature
D000475:Alkenes; D000588:Amines; D002264:Carboxylic Acids; D008024:Ligands; D012997:Solvents; D003300:Copper