Carbonylative N-Heterocyclization via Nitrogen-Directed C–C Bond Activation of Nonactivated Cyclopropanes
Adam D. J. Calow, David Dailler, John F. Bower
Abstract
Under Rh-catalyzed conditions, secondary amines and anilines function as directing groups to facilitate regioselective C-C bond activation of nonactivated cyclopropanes. The resulting amino-stabilized rhodacycles undergo carbonylative C-N bond formation en route to challenging seven- and eight-membered lactams. The processes represent rare examples where C-C bond oxidative addition of nonactivated cyclopropanes is exploited in reaction design.
Topics & Concepts
ChemistryRegioselectivityNitrogenOxidative phosphorylationCatalysisMedicinal chemistryStereochemistryOrganic chemistryBiochemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions