Organocatalyzed regio- and stereoselective diamination of functionalized alkenes

The first organocatalyzed diamination reaction of alkenes with N,N-dichlorotoluenesulfonamide (TsNCl2) and acetonitrile as nitrogen sources was reported. The catalytic diamination reaction was convenient to carry out, resulting in imidazoline products with good yields and excellent regio- and stereoselectivities. Several other organic molecules were also tried as catalyst for this reaction and good results were achieved. A new one-pot synthesis of vicinal diamines via the current PPh3-catalyzed diamination and the hydrolysis of resulting imidazoline products with SnCl4 as promoter was also established.

Graphical abstractA highly regio- and stereoselective organocatalyzed diamination reaction of alkenes with N,N-dichlorotoluenesulfonamide (TsNCl2) and acetonitrile as nitrogen sources was reported.Figure optionsDownload full-size imageDownload as PowerPoint slide