Rhodium‐Catalyzed Asymmetric Arylation of Cyclobutenone Ketals
David Egea‐Arrebola, F. Wieland Goetzke, Stephen P. Fletcher
Abstract
Complex cyclobutanes are important motifs in both bioactive molecules and natural products, yet their enantioselective preparation has not been widely explored. In this work, we describe rhodium-catalyzed enantioselective additions of aryl and vinyl boronic acids to cyclobutenone ketals. This transformation involves enantioselective carbometalation to give cyclobutyl-rhodium intermediates, followed by β-oxygen elimination to afford enantioenriched enol ethers. Overall, this addition serves as a surrogate for Rh-catalyzed 1,4-additions to cyclobutenone.
Topics & Concepts
RhodiumEnantioselective synthesisChemistryCatalysisCyclobutanesArylEnolOrganic chemistryCombinatorial chemistryStereoisomerismCycloadditionAlkylAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisCyclopropane Reaction Mechanisms