Sadhukhan, A., Hobbs, M.C., Meijer, A.J.H.M. et al. (1 more author) (2017) Highly enantioselective metallation–substitution alpha to a chiral nitrile. Chemical Science, 8 (2). pp. 1436-1441. ISSN 2041-6520
Abstract
We report the deprotonation of a chiral nitrile and reaction of the resulting chiral organometallic species with a variety of electrophiles to give highly enantiomerically enriched 2-substituted nitrile products. The nitrile was treated with TMPMgCl and the resulting anion, an asymmetric alpha cyano Grignard species, was found to be configurationally stable at low temperature for a short time (half-life several minutes at −104 °C).
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016 The Royal Society of Chemistry. This Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licence. |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Funding Information: | Funder Grant number EUROPEAN COMMISSION - FP6/FP7 ARNIIF - 625471 |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 15 Nov 2016 12:21 |
Last Modified: | 25 Oct 2018 08:57 |
Published Version: | http://dx.doi.org/10.1039/C6SC03712G |
Status: | Published |
Publisher: | Royal Society of Chemistry |
Refereed: | Yes |
Identification Number: | 10.1039/C6SC03712G |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:107280 |