Rhodium-Catalyzed Asymmetric Arylation of Cyclobutenone Ketals. 2023

David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
Department of Chemistry, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.

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.

UI MeSH Term Description Entries

Related Publications

David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
September 2010, Organic letters,
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
December 2020, Accounts of chemical research,
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
September 2010, Journal of the American Chemical Society,
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
June 2016, Organic letters,
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
March 2006, Organic & biomolecular chemistry,
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
December 2016, Organic letters,
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
October 2023, Angewandte Chemie (International ed. in English),
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
April 2022, Organic letters,
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
June 2017, Journal of the American Chemical Society,
David Egea-Arrebola, and F Wieland Goetzke, and Stephen P Fletcher
January 2017, Organic letters,
Copied contents to your clipboard!