Radical-mediated diamination of alkenes with phenylhydrazine and azodicarboxylates : highly diastereoselective synthesis of trans-diamines from cycloalkenes

Abstract

Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc=tert-butoxycarbonyl). This process works with the assistance of acetic acid by means of a radical mechanism and displays a high trans selectivity when cycloalkene substrates were used in the reaction.