Organic Chemistry Portal



Synthesis of Cyclic Guanidines via Silver-Catalyzed Intramolecular Alkene Hydroamination Reactions of N-Allylguanidines

Zachary J. Garlets, Mattia Silvi and John P. Wolfe*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States, Email:

Z. J. Garlets, M. Silvi, J. P. Wolfe, Org. Lett., 2016, 18, 2331-2334.

DOI: 10.1021/acs.orglett.6b00598

see article for more reactions


A silver-catalyzed hydroamination of tosyl-protected N-allylguanidines provides substituted cyclic guanidines in high yields. The reactions can be used for construction of quaternary stereocenters as well as both monocyclic and bicyclic guanidine products.

see article for more examples

Key Words

guanidines, N-heterocyles, oxygen

ID: J54-Y2016