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Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters
Item metadata
dc.contributor.author | Shu, Chang | |
dc.contributor.author | Liu, Honglei | |
dc.contributor.author | Slawin, Alexandra | |
dc.contributor.author | Carpenter-Warren, Cameron L. | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2019-11-15T13:30:04Z | |
dc.date.available | 2019-11-15T13:30:04Z | |
dc.date.issued | 2019-10-23 | |
dc.identifier | 261991297 | |
dc.identifier | 0e9bb6e1-1faa-4c61-b609-ed9384766ee0 | |
dc.identifier | 85076988829 | |
dc.identifier | 000503486800024 | |
dc.identifier.citation | Shu , C , Liu , H , Slawin , A , Carpenter-Warren , C L & Smith , A D 2019 , ' Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters ' , Chemical Science , vol. Advance Article . https://doi.org/10.1039/C9SC04303A | en |
dc.identifier.issn | 2041-6520 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/63716535 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/63716633 | |
dc.identifier.uri | https://hdl.handle.net/10023/18937 | |
dc.description | The research leading to these results (C. S., H. L.) has received funding from the Royal Society Newton Fellowship Programme. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. | en |
dc.description.abstract | The isothiourea-catalysed enantioselective Michael addition of 3-aryloxindole and 4-substituted-dihydropyrazol-3-one pronucleophiles to α,β-unsaturated p-nitrophenyl esters is reported. This process generates products containing two contiguous stereocentres, one quaternary, in good yields and excellent enantioselectivities (>30 examples, up to > 95 : 5 dr and 99 : 1 er). This protocol harnesses the multifunctional ability of p-nitrophenoxide to promote effective catalysis. In contrast to previous methodologies using tertiary amine Lewis bases, in which the pronucleophile was used as the solvent, this work allows bespoke pronucleophiles to be used in stoichiometric quantities. | |
dc.format.extent | 7 | |
dc.format.extent | 1161080 | |
dc.language.iso | eng | |
dc.relation.ispartof | Chemical Science | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | 10.1039/C9SC04303A | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | NF170330 | en |
dc.identifier.grantnumber | WM140071 | en |
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