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Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives
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dc.contributor.author | Bitai, Jacqueline | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Cordes, David B. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2020-05-28T09:30:04Z | |
dc.date.available | 2020-05-28T09:30:04Z | |
dc.date.issued | 2020-05-25 | |
dc.identifier.citation | Bitai , J , Slawin , A M Z , Cordes , D B & Smith , A D 2020 , ' Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives ' , Molecules , vol. 25 , no. 10 , 2463 . https://doi.org/10.3390/molecules25102463 | en |
dc.identifier.issn | 1420-3049 | |
dc.identifier.other | PURE: 268098165 | |
dc.identifier.other | PURE UUID: a40fb1f8-eaab-4964-9e75-75c8cb2e4c96 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/74872801 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/74872895 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/74872967 | |
dc.identifier.other | Scopus: 85085635491 | |
dc.identifier.other | WOS: 000539293400196 | |
dc.identifier.uri | https://hdl.handle.net/10023/20002 | |
dc.description | Funding: This research was funded by the School of Chemistry, University of St Andrews. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. | en |
dc.description.abstract | The scope and limitations of a tandem N-allylation/[2,3]-rearrangementprotocol are investigated through the incorporation of a variety of functionalgroups within an allylic phosphate precursor. This method uses readilyaccessible N,N-dimethylglycine aryl esters and functionalizedallylic phosphates, forming quaternary ammonium salts in situ in the presence of a palladium catalyst. Subsequentenantioselective [2,3]-sigmatropic rearrangement, promoted by the chiralisothiourea tetramisole, generates α-amino acid derivatives with two contiguousstereocenters. The incorporation of electron withdrawing ester and amide groupsgave the best results, furnishing the desired products in moderate to goodyields (29-70%), with low diastereocontrol (typically 60:40 dr) but highenantioselectivity (up to 90:10 er). These results indicate that substrate-catalystinteractions in the proposed transition state are sensitive to the substitutionpattern of the substrates. | |
dc.format.extent | 13 | |
dc.language.iso | eng | |
dc.relation.ispartof | Molecules | en |
dc.rights | Copyright © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). | en |
dc.subject | Isothiourea | en |
dc.subject | Palladium | en |
dc.subject | Enantioselective catalysis | en |
dc.subject | Amino acids | en |
dc.subject | [2,3]-rearrangement | en |
dc.subject | N-allylation | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Royal Society | 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.identifier.doi | https://doi.org/10.3390/molecules25102463 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | WM140071 | en |
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