Radical 1,2,3-tricarbofunctionalization of α-vinyl-β-ketoesters enabled by a carbon shift from an all-carbon quaternary center
Qi Zhang, Mong‐Feng Chiou, Changqing Ye, Xiao‐bing Yuan, Yajun Li, Hongli Bao
Abstract
the one-pot multifunctionalization of alkenes. This reaction allows the expansion of the carbon ring by a carbon shift from an all-carbon quaternary center, and enables further C-C bond formation on the tertiary carbon intermediate with the aim of reconstructing a new all-carbon quaternary center. The good functional group compatibility ensures diverse synthetic transformations of this method. Experimental and theoretical studies reveal that the excellent diastereoselectivity should be attributed to the hydrogen bonding between the substrates and solvent.
Topics & Concepts
Carbon fibersIntermolecular forceQuaternary carbonCompatibility (geochemistry)ChemistrySolventMoleculeTriple bondFunctional groupPolymer chemistryCatalysisOrganic chemistryMaterials scienceDouble bondEnantioselective synthesisComposite numberComposite materialPolymerCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques