Faculty, Staff and Student Publications
Language
English
Publication Date
3-20-2023
Journal
Angewandte Chemie International Edition
DOI
10.1002/anie.202217381
PMID
36728888
PMCID
PMC10946970
PubMedCentral® Posted Date
February 2023
PubMedCentral® Full Text Version
Post-print
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
Published Open-Access
yes
Recommended Citation
David Egea-Arrebola, F Wieland Goetzke, and Stephen P Fletcher, "Rhodium‐Catalyzed Asymmetric Arylation of Cyclobutenone Ketals" (2023). Faculty, Staff and Student Publications. 1624.
https://digitalcommons.library.tmc.edu/uthmed_docs/1624