Site-Selective C–H Functionalization of <i>N</i>-Aryl and <i>N</i>-Heteroaryl Piperidines, Morpholines, and Piperazines Controlled by a Chiral Dirhodium Tetracarboxylate Catalyst
Korkit Korvorapun, Yannick T. Boni, Thomas Maier, Armin Bauer, Thomas Licher, John E. Macor, Volker Derdau, Huw M. L. Davies
Abstract
Rhodium-catalyzed C–H insertion by donor/acceptor carbenes is a useful transformation in organic synthesis. However, the site-selectivity of the C–H transformation on the target molecule is often a major issue. Site-selective C–H functionalizations of challenging substrates like N -aryl- and N -heteroaryl piperidines could be achieved through chiral rhodium carbene intermediates, leading to the formation of highly stereoselective C-2 products. In addition, N -aryl morpholines and piperazines were selectively reacted at the α position to the N -aryl group.
Topics & Concepts
ArylRhodiumChemistryCarbeneCatalysisStereoselectivitySelectivitySurface modificationStereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryAlkylPhysical chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions