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Tandem palladium and isothiourea relay catalysis : enantioselective synthesis of α-amino acid derivatives via allylic amination and [2,3]-sigmatropic rearrangement
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dc.contributor.author | Spoehrle, Stephanie S. M. | |
dc.contributor.author | West, Thomas H. | |
dc.contributor.author | Taylor, James E. | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2017-08-28T14:30:11Z | |
dc.date.available | 2017-08-28T14:30:11Z | |
dc.date.issued | 2017-08-30 | |
dc.identifier.citation | Spoehrle , S S M , West , T H , Taylor , J E , Slawin , A M Z & Smith , A D 2017 , ' Tandem palladium and isothiourea relay catalysis : enantioselective synthesis of α-amino acid derivatives via allylic amination and [2,3]-sigmatropic rearrangement ' , Journal of the American Chemical Society , vol. 139 , no. 34 , pp. 11895-11902 . https://doi.org/10.1021/jacs.7b05619 | en |
dc.identifier.issn | 0002-7863 | |
dc.identifier.other | PURE: 250609895 | |
dc.identifier.other | PURE UUID: 78772293-59d7-4784-a0fc-3f2a06a25ab0 | |
dc.identifier.other | Scopus: 85028655880 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567475 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861713 | |
dc.identifier.other | WOS: 000409286000041 | |
dc.identifier.uri | https://hdl.handle.net/10023/11557 | |
dc.description | The research leading to these results (S.S.M.S.) has received funding from the European Union (Marie Curie ITN “SubiCat” PITN-GA-2013-607044) and the ERC under the European Union's Seventh Framework Programme (FP7/2007-2013)/E.R.C. grant agreement no 279850 (T.H.W., J.E.T.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. | en |
dc.description.abstract | A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity. | |
dc.format.extent | 8 | |
dc.language.iso | eng | |
dc.relation.ispartof | Journal of the American Chemical Society | en |
dc.rights | Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. | 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 | Tandem palladium and isothiourea relay catalysis : enantioselective synthesis of α-amino acid derivatives via allylic amination and [2,3]-sigmatropic rearrangement | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.sponsor | European Commission | en |
dc.contributor.sponsor | European Commission | en |
dc.description.version | Publisher PDF | 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/10.1021/jacs.7b05619 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | http://pubs.acs.org/doi/suppl/10.1021/jacs.7b05619 | en |
dc.identifier.grantnumber | WM140071 | en |
dc.identifier.grantnumber | SUBICAT | en |
dc.identifier.grantnumber | N/A | en |
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