New Alkene Difunctionalization Reactions for Organic Synthesis

August 24, 2018

Dr. John Wolfe

Photo: Seminar:

Profile: Dr. John Wolfe received his BA in Chemistry from the University of Colorado, Boulder, where he conducted undergraduate research in the labs of Professor Gary A. Molander. John Wolfe completed his Ph.D. in Organic Chemistry at the Massachusetts Institute of Technology under the guidance of Professor Stephen L. Buchwald. John Wolfe's thesis research was focused on metal-catalyzed C-N, C-O, and C-C bond-forming reactions of aryl halides, and involved the development of new reactions and novel catalysts. Following the completion of his Ph.D. in 1999, John Wolfe moved to the University of California, Irvine, where he conducted research as an NIH postdoctoral fellow in the labs of Professor Larry E. Overman. His postdoctoral research involved the development of new methods of synthesis of polycyclic guanidine derivatives and bicyclic ketones. Professor Wolfe joined the faculty at the University of Michigan in July, 2002. His current research is directed towards the development of new metal-catalyzed reactions for the synthesis of interesting, biologically active compounds. (website)

Abstract:  Two recently developed Pd-catalyzed alkene difunctionalization reactions will be described. The first involves the coupling of alkenes bearing pendant aryl/alkenyl triflate electrophiles with nitrogen-, oxygen-, or carbon-centered electrophiles to afford carbocyclic product. The second involves the coupling of N-allylureas or N-allylguanidines with  O-acylated hydroxylamines, which act as nitrogen centered electrophiles, to afford heterocyclic alkene diamination products. Details of the development, stereocontrol, and reaction mechanisms of these transformations will be discussed.

See Announcement