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Aryloxide-facilitated catalyst turnover in enantioselective α,β-unsaturated acyl ammonium catalysis
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dc.contributor.author | Matviitsuk, Anastassia | |
dc.contributor.author | Greenhalgh, Mark | |
dc.contributor.author | Barrios Antunez, Diego | |
dc.contributor.author | Slawin, Alexandra | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2017-08-28T09:30:08Z | |
dc.date.available | 2017-08-28T09:30:08Z | |
dc.date.issued | 2017-09-25 | |
dc.identifier | 250595435 | |
dc.identifier | 07e80960-f055-4c13-b392-dc46550a29a8 | |
dc.identifier | 85028361613 | |
dc.identifier.citation | Matviitsuk , A , Greenhalgh , M , Barrios Antunez , D , Slawin , A & Smith , A D 2017 , ' Aryloxide-facilitated catalyst turnover in enantioselective α,β-unsaturated acyl ammonium catalysis ' , Angewandte Chemie , vol. 129 , no. 40 , pp. 12450-12455 . https://doi.org/10.1002/ange.201706402 | en |
dc.identifier.issn | 0044-8249 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567474 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861809 | |
dc.identifier.uri | https://hdl.handle.net/10023/11551 | |
dc.description | The authors thank the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no. 279850 (A.D.S) and the EPSRC (EP/J018139/1, A.M.) for funding. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. | en |
dc.description.abstract | A new general concept for α,β-unsaturated acyl ammonium catalysis is reported that uses p-nitrophenoxide release from an α,β-unsaturated p-nitrophenyl ester substrate to facilitate catalyst turnover. This method was used for the enantioselective isothiourea-catalyzed Michael addition of nitroalkanes to α,β-unsaturated p-nitrophenyl esters in generally good yield and with excellent enantioselectivity (27 examples, up to 79% yield, 99:1 er). Mechanistic studies identified rapid and reversible catalyst acylation by the α,β-unsaturated p-nitrophenyl ester, and a recently reported variable-time normalization kinetic analysis method was used to delineate the complex reaction kinetics. | |
dc.format.extent | 6 | |
dc.format.extent | 986872 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie | en |
dc.subject | Lewis base catalysis | en |
dc.subject | α,β-unsaturated ammonium | en |
dc.subject | Isothiourea | en |
dc.subject | Aryloxide catalyst turnover | en |
dc.subject | Kinetic and mechanistic analysis | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | BDC | en |
dc.subject | R2C | en |
dc.subject.lcc | QD | en |
dc.title | Aryloxide-facilitated catalyst turnover in enantioselective α,β-unsaturated acyl ammonium catalysis | 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 | https://doi.org/10.1002/ange.201706402 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/J018139/1 | en |
dc.identifier.grantnumber | N/A | en |
dc.identifier.grantnumber | WM140071 | en |
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