Intramolecular N–Me and N–H aminoetherification for the synthesis of<i>N</i>-unprotected 3-amino-O-heterocycles
Mahesh P. Paudyal, Mingliang Wang, Juha H. Siitonen, Yimin Hu, Muhammed Yousufuddin, Hong C. Shen, John R. Falck, László Kürti
Abstract
A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a variety of 2,3-disubstituted aminoether O-heterocyclic scaffolds, including tetrahydrofurans, tetrahydropyrans and chromanes.
Topics & Concepts
AziridineIntramolecular forceDominoChemistryOlefin fiberRing (chemistry)Medicinal chemistryCatalysisStereochemistryOrganic chemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis