Nickel-Catalyzed Enantioselective Carbamoyl Iodination: A Surrogate for Carbamoyl Iodides
Austin D. Marchese, Marco Wollenburg, Bijan Mirabi, Xavier Abel‐Snape, Andrew Whyte, Frank Glorius, Mark Lautens
Abstract
This work reports the enantioselective formal transfer of a carbamoyl iodide across a 1,1-disubstituted styrene using Ni-catalysis. Employing an air-stable Ni(II) precatalyst and a commercially available chiral ligand ((S)-tBuPHOX), enantioenriched 3,3-disubstituted iodooxindoles were obtained in up to 90% yield and up to 97:3 e.r. This methodology was applied to the total synthesis of (−)-esermethole and (−)-phenserine.
Topics & Concepts
Enantioselective synthesisCatalysisYield (engineering)HalogenationNickelLigand (biochemistry)ChemistryIodideStyreneCombinatorial chemistryOrganic chemistryMaterials scienceCopolymerMetallurgyBiochemistryPolymerReceptorCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions