Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles
Haohua Huo, Bradley J. Paul-Gorsline, Gregory C. Fu
Abstract
2 pathways are limited in their ability to generate carbon-carbon bonds (inadequate scope, due to side reactions such as rearrangements and eliminations) and to control stereochemistry when beginning with readily available racemic starting materials (racemic products). Here, we report a chiral nickel catalyst that couples racemic electrophiles (propargylic halides) with racemic nucleophiles (β-zincated amides) to form carbon-carbon bonds in doubly stereoconvergent processes, affording a single stereoisomer of the product from two stereochemical mixtures of reactants.
Topics & Concepts
NucleophileElectrophileChemistryAlkylSN2 reactionOrganic chemistryAlkylationCatalysisOrganic synthesisCarbon fibersMedicinal chemistryCombinatorial chemistryMaterials scienceComposite numberComposite materialAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling ReactionsChemical Synthesis and Analysis