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Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N−H Insertion Reaction of Metallocarbenes with β-Aminoketone Derivatives

Nicolle, Simon M.; Lewis, William; Hayes, Christopher J.; Moody, Christopher J.

Authors

Simon M. Nicolle

William Lewis

CHRIS HAYES chris.hayes@nottingham.ac.uk
Professor of Organic Chemistry

Christopher J. Moody



Abstract

A highly stereoselective route to functionalized pyrrolidines from the metal catalyzed diverted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate and an iron(III)porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts with a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction.

Citation

Nicolle, S. M., Lewis, W., Hayes, C. J., & Moody, C. J. (2016). Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N−H Insertion Reaction of Metallocarbenes with β-Aminoketone Derivatives. Angewandte Chemie International Edition, 55(11), 3749-3753. https://doi.org/10.1002/anie.201511433

Journal Article Type Article
Acceptance Date Jan 19, 2016
Online Publication Date Feb 5, 2016
Publication Date Mar 7, 2016
Deposit Date Jul 14, 2016
Publicly Available Date Mar 28, 2024
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1433-7851
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 55
Issue 11
Pages 3749-3753
DOI https://doi.org/10.1002/anie.201511433
Keywords Aldol reaction; carbenes; diazo compounds; nitrogen heterocycles; transition-metal catalysis
Public URL https://nottingham-repository.worktribe.com/output/781243
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201511433/abstract
Additional Information This is the peer reviewed version of the following article: S. M. Nicolle, W. Lewis, C. J. Hayes, C. J. Moody. Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with ß-aminoketone derivatives. Angew. Chem. Int. Ed. 2016, 55, 3749-2753, doi:10.1002/anie.201511433, which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/anie.201511433/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving

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