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Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines
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dc.contributor.author | Smith, Siobhan Rose | |
dc.contributor.author | Fallan, Charlene | |
dc.contributor.author | Taylor, James Edward | |
dc.contributor.author | McLennan, Ross Sinclair | |
dc.contributor.author | Daniels, David Sydney Bernard | |
dc.contributor.author | Morrill, Louis Christian | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2015-07-24T10:10:01Z | |
dc.date.available | 2015-07-24T10:10:01Z | |
dc.date.issued | 2015-07-13 | |
dc.identifier | 184426478 | |
dc.identifier | bc5a8d9a-5cdb-49b7-b005-15f0fe83f974 | |
dc.identifier | 84934299973 | |
dc.identifier | 000357328200036 | |
dc.identifier.citation | Smith , S R , Fallan , C , Taylor , J E , McLennan , R S , Daniels , D S B , Morrill , L C , Slawin , A M Z & Smith , A D 2015 , ' Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines ' , Chemistry - A European Journal , vol. 21 , no. 29 , pp. 10530–10536 . https://doi.org/10.1002/chem.201501271 | en |
dc.identifier.issn | 0947-6539 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567498 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861552 | |
dc.identifier.uri | https://hdl.handle.net/10023/7021 | |
dc.description | The authors thank the Royal Society for a University Research Fellowship (A.D.S.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007—2013), ERC Grant Agreement No. 279850 (C.F. and J.E.T.), GSK (CASE award to S.R.S.) and EPSRC grant No. EP/J018139/1 (D.S.B.D.) for funding. | en |
dc.description.abstract | A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high dr, yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks. | |
dc.format.extent | 580433 | |
dc.language.iso | eng | |
dc.relation.ispartof | Chemistry - A European Journal | en |
dc.subject | Organocatalysis | en |
dc.subject | Nitrogen heterocycles | en |
dc.subject | Oxygen heterocycles | en |
dc.subject | Asymmetric synthesis | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1002/chem.201501271 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | http://onlinelibrary.wiley.com/doi/10.1002/chem.201501271/suppinfo | en |
dc.identifier.grantnumber | EP/J018139/1 | en |
dc.identifier.grantnumber | EP/J018139/1 | en |
dc.identifier.grantnumber | EP/K031252/1 | en |
dc.identifier.grantnumber | EP/K039210/1 | en |
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