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Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides
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dc.contributor.author | West, Thomas H. | |
dc.contributor.author | Spoehrle, Stéphanie S. M. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2018-01-31T00:31:34Z | |
dc.date.available | 2018-01-31T00:31:34Z | |
dc.date.issued | 2017-07-20 | |
dc.identifier | 249036825 | |
dc.identifier | ff39a291-b4c9-4ddc-9455-46f06d19a635 | |
dc.identifier | 85013441087 | |
dc.identifier | 000405158400015 | |
dc.identifier.citation | West , T H , Spoehrle , S S M & Smith , A D 2017 , ' Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N , N -diallyl allylic ammonium ylides ' , Tetrahedron , vol. 73 , no. 29 , pp. 4138-4149 . https://doi.org/10.1016/j.tet.2017.01.062 | en |
dc.identifier.issn | 0040-4020 | |
dc.identifier.other | RIS: urn:0E61E9C036C60511338C857E4F9FD3AF | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567476 | |
dc.identifier.uri | https://hdl.handle.net/10023/12636 | |
dc.description | The research leading to these results (T.H.W.) has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007–2013)/E.R.C. grant agreement n° 279850 and the European Union (Marie Curie ITN “SubiCat” PITN-GA-2013-607044) (S. S. M. S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. The data underpinning this publication can be found at DOI: http://dx.doi.org/10.17630/f522b48d-ed02–42b3-a161-54687ea5af57 | en |
dc.description.abstract | The isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangement of N,N-diallyl allylic ammonium ylides is explored as a key part of a route to free functionalised α-amino esters and piperidines. The [2,3]-sigmatropic rearrangement proceeds with excellent diastereo- and enantiocontrol (>95:5 dr, up to 97% ee), with the resultant N,N-diallyl α-amino esters undergoing either mono- or bis-N-allyl deprotection. Bis-N-allyl deprotection leads to free α-amino esters, while the mono-deprotection strategy has been utilized in the synthesis of a target functionalised piperidine. | |
dc.format.extent | 12 | |
dc.format.extent | 785356 | |
dc.language.iso | eng | |
dc.relation.ispartof | Tetrahedron | en |
dc.subject | [2,3]-rearrangement | en |
dc.subject | Isothiourea catalysis | en |
dc.subject | Allylic ammonium ylides | en |
dc.subject | Enantioselective catalysis | en |
dc.subject | α-amino esters | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides | en |
dc.type | Journal article | en |
dc.contributor.sponsor | European Commission | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.sponsor | European Commission | 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 | 10.1016/j.tet.2017.01.062 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2018-01-30 | |
dc.identifier.url | http://www.sciencedirect.com/science/article/pii/S0040402017300972#appd001 | en |
dc.identifier.grantnumber | SUBICAT | en |
dc.identifier.grantnumber | WM140071 | en |
dc.identifier.grantnumber | N/A | en |
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