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An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles : generality, applications and mechanistic investigations
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dc.contributor.author | Richmond, Edward | |
dc.contributor.author | Ling, Kenneth Bruce | |
dc.contributor.author | Duguet, Nicolas Fabien Denis | |
dc.contributor.author | Manton, Lois B. | |
dc.contributor.author | Çelebi-Ölçüm, Nihan | |
dc.contributor.author | Lam, Yu-hong | |
dc.contributor.author | Alsancak, Sezen | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Houk, K. N. | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2015-12-03T00:11:28Z | |
dc.date.available | 2015-12-03T00:11:28Z | |
dc.date.issued | 2015-02-14 | |
dc.identifier | 159434783 | |
dc.identifier | 84837478-b71a-4cd2-ae3c-34376f9884d2 | |
dc.identifier | 84921994301 | |
dc.identifier | 000349032400026 | |
dc.identifier | 25501712 | |
dc.identifier.citation | Richmond , E , Ling , K B , Duguet , N F D , Manton , L B , Çelebi-Ölçüm , N , Lam , Y , Alsancak , S , Slawin , A M Z , Houk , K N & Smith , A D 2015 , ' An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles : generality, applications and mechanistic investigations ' , Organic & Biomolecular Chemistry , vol. 13 , no. 6 , pp. 1807-1817 . https://doi.org/10.1039/c4ob02526a | en |
dc.identifier.issn | 1477-0520 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567502 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861322 | |
dc.identifier.uri | https://hdl.handle.net/10023/7881 | |
dc.description | The authors thank the Royal Society for a URF (ADS), Cancer Research UK (ER), the Leverhulme Trust (ND) and EPSRC (KBL) for funding. We are also grateful to the National Science Foundation (USA) for financial support of the research at UCLA (KNH). | en |
dc.description.abstract | The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology. | |
dc.format.extent | 11 | |
dc.format.extent | 3856839 | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic & Biomolecular Chemistry | en |
dc.subject | Amino acids | en |
dc.subject | Anti-cancer agents | en |
dc.subject | Cascade process | en |
dc.subject | Computational investigation | en |
dc.subject | L-serine | en |
dc.subject | Potential utility | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | SDG 3 - Good Health and Well-being | en |
dc.subject.lcc | QD | en |
dc.title | An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles : generality, applications and mechanistic investigations | en |
dc.type | Journal article | 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 | 10.1039/c4ob02526a | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2015-12-03 | |
dc.identifier.grantnumber | EP/E03795X/1 | en |
dc.identifier.grantnumber | EP/K039210/1 | en |
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