Three-Component 1,2-Carboamidation of Bridged Bicyclic Alkenes via Rh<sup>III</sup>-Catalyzed Addition of C–H Bonds and Amidating Reagents
Daniel S. Brandes, Ana Sirvent, Brandon Q. Mercado, Jonathan A. Ellman
Abstract
A three-component method is described for the preparation of syn-1,2-disubstituted bridged bicyclic compounds. The reaction was demonstrated for readily available aromatic and heteroaromatic C–H bond substrates with tertiary and secondary amide, lactam, pyrazole, and triazole directing groups and a variety of bridged bicyclic alkenes, including norbornene, benzonorbornadiene, oxygen- and nitrogen-bridged analogs, and an unsaturated tropinone. A broad dioxazolone scope was also observed. The use of a chiral Cp-derived RhIII catalyst enables asymmetric synthesis of products.
Topics & Concepts
Bicyclic moleculeChemistryNorborneneCatalysisAmideReagentStereochemistryCombinatorial chemistryOrganic chemistryPolymerizationPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis