Enantioselective Synthesis of Tertiary β‐Boryl Amides by Conjunctive Cross‐Coupling of Alkenyl Boronates and Carbamoyl Chlorides
Christopher A. Wilhelmsen, Xuntong Zhang, Jesse A. Myhill, James P. Morken
Abstract
Synthesis of versatile β tert-boryl amides is accomplished by conjunctive cross-coupling of α-substituted alkenyl boron "ate" complexes and carbamoyl chloride electrophiles. This reaction can be accomplished in an enantioselective fashion using a palladium catalyst in combination with MandyPhos. The addition of water results in enhanced chemoselectivity for the conjunctive coupling product relative to the Suzuki-Miyaura cross-coupling product. Transformations of the reaction products were examined as well as application to the synthesis of (+)-adalinine.
Topics & Concepts
ChemoselectivityEnantioselective synthesisChemistryElectrophileCatalysisCoupling (piping)Organic chemistryCombinatorial chemistryAlkylationMaterials scienceMetallurgyOrganoboron and organosilicon chemistryAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and Catalysis