Rhodium-Catalyzed Asymmetric Arylation of Cyclobutenone Ketals

Authors

David Egea-Arrebola
F Wieland Goetzke
Stephen P Fletcher

Publication Date

3-20-2023

Journal

Angewandte Chemie International Edition

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.

Keywords

Arylboronic Acids, Asymmetric Catalysis, Complex Cyclobutanes, Cyclobutenone, Rhodium