Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives

Nicolle, Simon M. and Lewis, William and Hayes, Christopher J. and Moody, Christopher J. (2016) Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives. Angewandte Chemie International Edition, 55 (11). pp. 3749-3753. ISSN 1433-7851

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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.

Item Type: Article
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 β-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
Keywords: Aldol reaction; carbenes; diazo compounds; nitrogen heterocycles; transition-metal catalysis
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1002/anie.201511433
Depositing User: Bramwell, Roseanna
Date Deposited: 14 Jul 2016 14:55
Last Modified: 06 Feb 2017 04:43
URI: http://eprints.nottingham.ac.uk/id/eprint/34962

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