Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides

Allylic sulfamides undergo efficient aerobic oxidative cyclization at room temperature, mediated by a new Pd catalyst system consisting of 5% Pd(TFA)(2)/10% DMSO in THF. The synthetic utility of these reactions is enhanced by several features: (1) the sulfamide substrates are accessible in multi-gram scale from the corresponding allylic and primary amines, (2) the cyclic sulfamide products are readily converted to the corresponding 1,2-diamines upon treatment with LiAlH(4), and (3) substrates derived from chiral allylic amines cyclize with very high levels of diastereoselectivity.