Copper-Catalyzed Oxidative Dimerizations of 3-N-Hydroxy-aminoprop-1-enes to Form 1,4-Dihydroxy-2,3-diaminocyclohexanes with C2 Symmetry.

This work describes the one-step construction of complex and important molecular frameworks through copper-catalyzed oxidations of cheap tertiary amines. Copper-catalyzed aerobic oxidations of N-hydroxyaminopropenes to form C2-symmetric N- and O-functionalized cyclohexanes are described. Such catalytic oxidations proceed with remarkable stereocontrol and high efficiency. Reductive cleavage of the two NO bonds of these products delivers 1,4-dihydroxy-2,3-diaminocyclohexanes, which are important skeletons of several bioactive molecules.