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Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition
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dc.contributor.author | Neyyappadath, Rifahath M. | |
dc.contributor.author | Greenhalgh, Mark D. | |
dc.contributor.author | Cordes, David Bradford | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2020-04-11T23:32:32Z | |
dc.date.available | 2020-04-11T23:32:32Z | |
dc.date.issued | 2019-04-12 | |
dc.identifier | 258321100 | |
dc.identifier | d3db96fd-fb3b-443a-a8ce-b8a5feaee705 | |
dc.identifier | 85064529012 | |
dc.identifier | 000483709700015 | |
dc.identifier.citation | Neyyappadath , R M , Greenhalgh , M D , Cordes , D B , Slawin , A M Z & Smith , A D 2019 , ' Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition ' , European Journal of Organic Chemistry , vol. Early View . https://doi.org/10.1002/ejoc.201900326 | en |
dc.identifier.issn | 1434-193X | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/56638868 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/56638869 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861816 | |
dc.identifier.uri | https://hdl.handle.net/10023/19785 | |
dc.description | We thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, R.M.N.) for funding. We thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850 (A.D.S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Service at Swansea. The research data supporting this publication can be accessed at https://doi.org/10.17630/00aff760-0732-438f-a9d1-30c7cf3a87a0 | en |
dc.description.abstract | A serendipitously-discovered process for the synthesis of heterocyclic products containing a novel fused indoline-cyclobutanone ring system is reported. This process is believed to take place through in situ generation of a ketene intermediate, followed by intramolecular [2+2] cycloaddition with a pendant enamide. The formation of a ketene intermediate in this process is significant as the reaction conditions employed are analogous to those commonly used in tertiary amine Lewis base catalysis, where the potential intermediacy of ketenes is an important consideration that is often overlooked. | |
dc.format.extent | 1560259 | |
dc.language.iso | eng | |
dc.relation.ispartof | European Journal of Organic Chemistry | en |
dc.subject | Lewis base catalysis | en |
dc.subject | Ketene | en |
dc.subject | [2+2]-cycloaddition | en |
dc.subject | N-heterocycles | en |
dc.subject | Indoline-cyclobutanone | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | European Commission | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | 10.1002/ejoc.201900326 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2020-04-12 | |
dc.identifier.grantnumber | EP/L016419/1 | en |
dc.identifier.grantnumber | N/A | en |
dc.identifier.grantnumber | WM140071 | en |
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