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Nicolle, Simon M., Lewis, William, 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
RIS ID:	https://nottingham-repository.worktribe.com/output/781243
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:	10.1002/anie.201511433
Depositing User:	Bramwell, Roseanna
Date Deposited:	14 Jul 2016 14:55
Last Modified:	04 May 2020 17:42
URI:	https://eprints.nottingham.ac.uk/id/eprint/34962

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