Alshawish, M.R., Barker, G., Measom, N.D. et al. (1 more author) (2016) Metallation–substitution of an α-oxygenated chiral nitrile. Comptes Rendus Chimie. ISSN 1631-0748
Abstract
Deprotonation of a chiral alpha-oxygenated nitrile with the base 2,2,6,6-tetramethylpiperidylmagnesium chloride, TMPMgCl, gives rise to a chiral magnesiated nitrile, and this anion has sufficient configurational stability at low temperature to allow the formation of highly enantiomerically enriched substituted nitrile products after electrophilic quench.
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Copyright, Publisher and Additional Information: | © 2016 Académie des sciences. Published by Elsevier Masson SAS. This is an author produced version of a paper subsequently published in Comptes Rendus Chimie. Uploaded in accordance with the publisher's self-archiving policy. Article available under the terms of the CC-BY-NC-ND licence (https://creativecommons.org/licenses/by-nc-nd/4.0/) | ||||
Keywords: | Alkylation; Asymmetric synthesis; Carbanions; Enantioselectivity; Magnesium; Metallation; Synthetic methods | ||||
Dates: |
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Institution: | The University of Sheffield | ||||
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) | ||||
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Depositing User: | Symplectic Sheffield | ||||
Date Deposited: | 10 Jan 2017 13:56 | ||||
Last Modified: | 21 Dec 2017 01:38 | ||||
Published Version: | https://doi.org/10.1016/j.crci.2016.11.006 | ||||
Status: | Published online | ||||
Publisher: | Elsevier Masson | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1016/j.crci.2016.11.006 |
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