Enantio- and Chemoselective Intramolecular Iridium-Catalyzed <i>O</i>-Allylation of Oximes
Tobias Sandmeier, Erick M. Carreira
Abstract
-allylation of oximes is described. Kinetic resolution in an intramolecular setting provides enantioenriched oxime ethers and aliphatic allylic alcohols. The synthetic potential of the products generated with this method is showcased by their elaboration into a series of heterocyclic compounds and the formal synthesis of glycoprotein GP IIb-IIIa receptor antagonist (-)-roxifiban. Preliminary mechanistic experiments and computational data shed light on the remarkable chemoselectivity of the reaction.
Topics & Concepts
ChemistryIntramolecular forceIridiumCatalysisCombinatorial chemistryOrganic chemistryStereochemistryChemical Synthesis and ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis