Substrate and catalyst effects in the enantioselective copper catalysed C–H insertion reactions of α-diazo-β-oxo sulfones

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dc.contributor.author Maguire, Anita R.
dc.contributor.author Shiely, Amy E.
dc.contributor.author Clarke, Leslie-Ann
dc.contributor.author Flynn, Christopher J.
dc.contributor.author Buckley, Aoife
dc.contributor.author Ford, Alan
dc.contributor.author Lawrence, Simon E.
dc.date.accessioned 2018-04-04T11:10:50Z
dc.date.available 2018-04-04T11:10:50Z
dc.date.issued 2018-03-23
dc.identifier.citation Maguire, A. R., Shiely, A., Clarke, L. A., Flynn, C., Buckley, A., Ford, A. and Lawrence, S. E. (2018) 'Substrate and catalyst effects in the enantioselective copper catalysed C–H insertion reactions of α-diazo-β-oxo sulfones', European Journal of Organic Chemistry. doi:10.1002/ejoc.201800077 en
dc.identifier.issn 1099-0690
dc.identifier.issn 1434-193X
dc.identifier.uri http://hdl.handle.net/10468/5732
dc.identifier.doi 10.1002/ejoc.201800077
dc.description.abstract Excellent enantioselectivities of up to 98% ee are achieved employing the copper‐bis(oxazoline)‐NaBARF catalyst system in the C‐H insertion reactions of α‐diazo‐β‐oxo sulfones. The influence of variation of the bis(oxazoline) ligand, copper salt, additive and substrate on both the efficiency and the enantioselectivities of these intramolecular C‐H insertion reactions has been explored. Optimum enantioselectivities are achieved with the phenyl and diphenyl ligands across the substrate series. en
dc.description.sponsorship Irish Research Council (Project Numbers GOIPG/2013/1064 and GOIPG/2013/225); Science Foundation Ireland (Grant Number 02/PICA/B802/EC07) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher John Wiley & Sons, Inc. en
dc.rights © 2018, WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: Maguire, A. R., Shiely, A., Clarke, L. A., Flynn, C., Buckley, A., Ford, A. and Lawrence, S. E. (2018) 'Substrate and catalyst effects in the enantioselective copper catalysed C–H insertion reactions of α-diazo-β-oxo sulfones', European Journal of Organic Chemistry, which has been published in final form at http://dx.doi.org/10.1002/ejoc.201800077 This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. en
dc.subject Copper catalysis en
dc.subject bis(oxazoline) ligands en
dc.subject Asymmetric C-H insertion en
dc.subject α-Diazocarbonyl compounds en
dc.subject α-Diazo-β-oxo sulfones en
dc.title Substrate and catalyst effects in the enantioselective copper catalysed C–H insertion reactions of α-diazo-β-oxo sulfones en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Anita Maguire, Vice President For Research, University College Cork, Cork, Ireland. +353-21-490-3000 Email: a.maguire@ucc.ie en
dc.internal.availability Full text available en
dc.check.info Access to this article is restricted until 12 months after publication by request of the publisher. en
dc.check.date 2019-03-23
dc.date.updated 2018-04-03T08:54:32Z
dc.description.version Accepted Version en
dc.internal.rssid 432431789
dc.internal.rssid 432558350
dc.internal.rssid 432558357
dc.contributor.funder Irish Research Council en
dc.contributor.funder Irish Research Council for Science, Engineering and Technology en
dc.contributor.funder Janssen Pharmaceuticals en
dc.contributor.funder Science Foundation Ireland en
dc.description.status Peer reviewed en
dc.identifier.journaltitle European Journal of Organic Chemistry en
dc.internal.copyrightchecked Yes en
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress a.maguire@ucc.ie en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en
dc.internal.bibliocheck In Press. Check for vol. / issue / page range / supplementary files. Amend citation as necessary.


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