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Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid : two-step synthesis of stereodefined dihydroindolizinones
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dc.contributor.author | Zhang, Shuyue | |
dc.contributor.author | Taylor, James Edward | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2019-08-23T23:39:38Z | |
dc.date.available | 2019-08-23T23:39:38Z | |
dc.date.issued | 2018-08-24 | |
dc.identifier.citation | Zhang , S , Taylor , J E , Slawin , A M Z & Smith , A D 2018 , ' Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid : two-step synthesis of stereodefined dihydroindolizinones ' , Organic Letters , vol. In press . https://doi.org/10.1021/acs.orglett.8b02423 | en |
dc.identifier.issn | 1523-7060 | |
dc.identifier.other | PURE: 255537851 | |
dc.identifier.other | PURE UUID: 895e5f32-1691-47cb-a00d-70a13b8de9ba | |
dc.identifier.other | Scopus: 85053018460 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/47928965 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861415 | |
dc.identifier.other | WOS: 000444527000092 | |
dc.identifier.uri | https://hdl.handle.net/10023/18368 | |
dc.description | JET thanks The Leverhulme Trust for an Early Career Fellowship [ECF-2014-005]. ADS thanks the Royal Society for a Wolfson Research Merit Award. | en |
dc.description.abstract | Catalytic enantioselective functionalization of 2-pyrrolyl acetic acid with trichloromethyl enones using isothiourea catalysis is reported, leading to a range of stereodefined diesters and diamides after nucleophilic ring-opening with either methanol or benzylamine (30 examples, up to >95:5 dr and >99:1 er). Subsequent intramolecular Friedel-Crafts reaction allows access to dihydroindolizinones in high yields and stereofidelity (6 examples, up to >95:5 dr and 99:1 er). | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic Letters | en |
dc.rights | Copyright © 2018 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/acs.orglett.8b02423 | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid : two-step synthesis of stereodefined dihydroindolizinones | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Leverhulme Trust | en |
dc.contributor.sponsor | The Royal Society | en |
dc.description.version | Postprint | 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/acs.orglett.8b02423 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-08-24 | |
dc.identifier.url | https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.8b02423 | en |
dc.identifier.grantnumber | ECF-2014-005 | en |
dc.identifier.grantnumber | WM140071 | en |
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