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

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

Authors

Jonathan Day

Ben McKeever-Abbas



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 http://eprints.nottingham.ac.uk/id/eprint/31460
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201511047/full
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
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

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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