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Unanticipated silyl transfer in enantioselective α,β-unsaturated acyl ammonium catalysis using silyl nitronates
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dc.contributor.author | Matviitsuk, Anastassia | |
dc.contributor.author | Greenhalgh, Mark David | |
dc.contributor.author | Taylor, James E. | |
dc.contributor.author | Nguyen, Xuan B. | |
dc.contributor.author | Cordes, David Bradford | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Lupton, David W. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2020-12-23T00:37:24Z | |
dc.date.available | 2020-12-23T00:37:24Z | |
dc.date.issued | 2019-12-23 | |
dc.identifier.citation | Matviitsuk , A , Greenhalgh , M D , Taylor , J E , Nguyen , X B , Cordes , D B , Slawin , A M Z , Lupton , D W & Smith , A D 2019 , ' Unanticipated silyl transfer in enantioselective α,β-unsaturated acyl ammonium catalysis using silyl nitronates ' , Organic Letters , vol. Article ASAP . https://doi.org/10.1021/acs.orglett.9b04404 | en |
dc.identifier.issn | 1523-7060 | |
dc.identifier.other | PURE: 264666865 | |
dc.identifier.other | PURE UUID: 729939de-17b7-42b9-b0c5-2802860c1b57 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/66591728 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/66591773 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/66591814 | |
dc.identifier.other | Scopus: 85077476696 | |
dc.identifier.other | WOS: 000506088700069 | |
dc.identifier.uri | https://hdl.handle.net/10023/21187 | |
dc.description | We thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013), ERC Grant Agreement 279850 (A.D.S.), the EPSRC (EP/J018139/1, A.M.), and the Royal Society of Chemistry (Researcher Mobility Grant). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. D.W.L. thanks the Australian Research Council for a Discovery Award (DP170103567). We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University. | en |
dc.description.abstract | The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of γ-nitro-substituted silyl esters containing up to two contiguous stereocenters in good yields with excellent enantioselectivities (up to 93% yield and 99:1 er). The serendipitously discovered formation of silyl ester products in this reaction demonstrates a novel platform for catalyst turnover in α,β-unsaturated acyl ammonium catalysis. | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic Letters | en |
dc.rights | Copyright © 2019 American Chemical Society. his work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/acs.orglett.9b04404 | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Unanticipated silyl transfer in enantioselective α,β-unsaturated acyl ammonium catalysis using silyl nitronates | en |
dc.type | Journal article | en |
dc.contributor.sponsor | European Commission | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | The Royal Society | en |
dc.description.version | Postprint | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1021/acs.orglett.9b04404 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2020-12-23 | |
dc.identifier.grantnumber | N/A | en |
dc.identifier.grantnumber | EP/J018139/1 | en |
dc.identifier.grantnumber | WM140071 | en |
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