A novel traceless resin-bound guanidinylating reagent for secondary amines to prepare N,N-disubstituted guanidines.
[reaction: see text]. We report the development of a solid support-linked guanidinylating reagent. This reagent consists of a urethane-protected triflyl guanidine attached to the resin via a carbamate linker. It allows for rapid synthesis of guanidines from a variety of amines. It provides access to N-alkyl/aryl- or N,N-dialkylguanidines under mild conditions. Cleavage with 50% TFA produces target molecules in high yields and purity. The ability to guanidinylate secondary amines is a significant feature of this guanidinylating reagent.
Zapf
C W
CW
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0343, USA.
Creighton
C J
CJ
Tomioka
M
M
Goodman
M
M
D000588:Amines / Q000737:chemistry*; D019791:Guanidine / Q000138:chemical synthesis* / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D014520:Urethane / Q000737:chemistry
D000588:Amines; D006146:Guanidines; D014520:Urethane; D019791:Guanidine