Iridium-Catalyzed Enantioconvergent Allylation of a Boron-Stabilized Organozinc Reagent
Panchi Guo, Miao Zhan
Abstract
An iridium-catalyzed enantioconvergent coupling of the versatile boron-stabilized organozinc reagent BpinCH2ZnI with a racemic branched allylic carbonate has been developed here, which differs from our previous work by using 1,1-bisborylmethane through the kinetic resolution process. The reaction has a broad substrate scope, and various chiral homoallylic organoboronic esters could be obtained in good yields with excellent enantioselectivities. The synthetic practicability of the products was demonstrated by their conversion to other useful families of compounds.
Topics & Concepts
ReagentKinetic resolutionIridiumCatalysisChemistryAllylic rearrangementSubstrate (aquarium)BoronOrganic chemistryCombinatorial chemistryCoupling reactionEnantioselective synthesisGeologyOceanographyOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisCatalytic Cross-Coupling Reactions