Enantioselective Construction of Carbocyclic and Heterocyclic Tertiary Boronic Esters by Conjunctive Cross-Coupling Reaction
Xuntong Zhang, Chenpeng Gao, James P. Morken
Abstract
Synthesis of stereodefined carbocyclic and heterocyclic tertiary boronic esters is accomplished by performing a conjunctive cross-coupling reaction on preformed cyclic boron ate complexes. Boronates bearing spirocyclic and aryl bicyclic skeletons can be synthesized enantioselectively using a chiral PHOX-ligated Pd catalyst with achiral starting material, while substrates bearing continuous stereogenic centers can be generated diastereoselectively. A variety of aryl and alkenyl electrophiles are incorporated.
Topics & Concepts
StereocenterChemistryEnantioselective synthesisArylElectrophileBoronic acidOrganic chemistryCatalysisBoronBicyclic moleculeCombinatorial chemistryStereochemistryAlkylOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisCatalytic Cross-Coupling Reactions