Stereoselective Synthesis of Tetrahydroindolizines through the Catalytic Formation of Pyridinium Ylides from Diazo Compounds

Day, Jonathan; McKeever-Abbas, Ben; Dowden, James

Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Commercially available iron(III) and copper(I) complexes catalyzed multicomponent cycloaddition reactions between diazo compounds, pyridines, and electrophilic alkenes to give alkaloid-inspired tetrahydroindolizidines in high yield with high diastereoselectivity. Hitherto, the catalytic formation of versatile pyridinium ylides from metal carbenes has been poorly developed; the broad utility demonstrated herein sets the stage for the invention of further multicomponent reactions in future.

Citation

Day, J., McKeever-Abbas, B., & Dowden, J. (2016). Stereoselective Synthesis of Tetrahydroindolizines through the Catalytic Formation of Pyridinium Ylides from Diazo Compounds. Angewandte Chemie International Edition, 55(19), 5809-5813. https://doi.org/10.1002/anie.201511047

• Journal Article Type: Article
• Acceptance Date: Jan 15, 2016
• Online Publication Date: Apr 5, 2016
• Publication Date: May 4, 2016
• Deposit Date: Feb 1, 2016
• Publicly Available Date: Apr 8, 2016
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 55
• Issue: 19
• Pages: 5809-5813
• DOI: https://doi.org/10.1002/anie.201511047
• Keywords: carbenes; cycloaddition; diazo compounds; homogenous catalysis; pyridinium ylides
• Public URL: https://nottingham-repository.worktribe.com/output/783814
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201511047/full
• Additional Information: This is the pre-peer reviewed version of the following article: J. Day, B. McKeever-Abbas, J. Dowden, Angew. Chem. Int. Ed. 2016, 55, 5809, which has been published in final form at doi:10.1002/anie.201511047
• Contract Date: Feb 1, 2016