Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters
Jianyu Xu, Olivia P. Bercher, Mary P. Watson
Abstract
The use of a simple stilbene ligand has enabled a stereospecific Suzuki-Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an important breakthrough in the "naphthyl requirement" that pervades stereospecific cross-couplings involving enantioenriched electrophiles.
Topics & Concepts
StereocenterStereospecificityChemistryElectrophileYield (engineering)Quaternary carbonStereochemistryLigand (biochemistry)Combinatorial chemistryEnantioselective synthesisOrganic chemistryCatalysisBiochemistryMetallurgyMaterials scienceReceptorCatalytic Cross-Coupling ReactionsChemical synthesis and alkaloidsSynthetic Organic Chemistry Methods