Synthesis of bicyclic guanidines via cascade hydroamination/Michael additions of mono-N-acryloylpropargylguanidines.
A cascade silver(I)-catalyzed hydroamination/Michael addition sequence has been developed to deliver highly substituted bicyclic guanidines. This transformation gives rise to geometrically and constitutionally stable ene-guanidines and generates a remote stereocenter with moderate to high diastereoselectivity.
†Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States.
Ki-Hyeok
KH
Kwon
†Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States.
Catherine M
CM
Serrano
‡Department of Pharmacy/Toxicology, University of Utah, 30 South 2000 East, Salt Lake City, Utah 84112 United States.
Michael
M
Koch
‡Department of Pharmacy/Toxicology, University of Utah, 30 South 2000 East, Salt Lake City, Utah 84112 United States.
Louis R
LR
Barrows
†Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States.
Ryan E
RE
Looper
D002384:Catalysis; D003500:Cyclization; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
D006146:Guanidines; D012834:Silver