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Evaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonisations
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dc.contributor.author | Young, Claire M. | |
dc.contributor.author | Taylor, James E. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2020-04-10T23:32:10Z | |
dc.date.available | 2020-04-10T23:32:10Z | |
dc.date.issued | 2019-05-21 | |
dc.identifier | 258563119 | |
dc.identifier | e85c986f-599c-4da7-b2c9-222cac72c267 | |
dc.identifier | 85065861147 | |
dc.identifier | 000468000000009 | |
dc.identifier.citation | Young , C M , Taylor , J E & Smith , A D 2019 , ' Evaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonisations ' , Organic & Biomolecular Chemistry , vol. 17 , no. 19 , pp. 4747-4752 . https://doi.org/10.1039/C9OB00703B | en |
dc.identifier.issn | 1477-0520 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/56424214 | |
dc.identifier.uri | https://hdl.handle.net/10023/19781 | |
dc.description | We thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement no. 279850 (CMY, JET). ADS thanks the Royal Society for a Wolfson Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University. The data underpinning this research can be found at DOI: https://doi.org/10.17630/cb133261-b58e-4d72-b380-c877c993dc5d | en |
dc.description.abstract | An evaluation of a range of aryl, alkyl and vinyl esters as prospective C(1)-ammonium enolate precursors in enantioselective Michael addition-lactonisation processes with (E)-trifluoromethylenones using isothiourea catalysis is reported. Electron deficient aryl esters are required for reactivity, with 2,4,6-trichlorophenyl esters providing optimal product yields. Catalyst screening showed that tetramisole was the most effective isothiourea catalyst, giving the desired dihydropyranone product in excellent yield and stereoselectivity (up to 90:10 dr and 98:2 er). The scope and limitations of this process have been evaluated, with a range of diester products being generated after ring-opening with MeOH to give stereodefined dihydropyranones with excellent stereocontrol (10 examples, typically ~90:10 dr and >95:5 er). | |
dc.format.extent | 481339 | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic & Biomolecular Chemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Evaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonisations | en |
dc.type | Journal article | 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 | 10.1039/C9OB00703B | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2020-04-11 | |
dc.identifier.grantnumber | N/A | en |
dc.identifier.grantnumber | WM140071 | en |
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