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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.authorZhang, Shuyue
dc.contributor.authorTaylor, James Edward
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2019-08-23T23:39:38Z
dc.date.available2019-08-23T23:39:38Z
dc.date.issued2018-08-24
dc.identifier255537851
dc.identifier895e5f32-1691-47cb-a00d-70a13b8de9ba
dc.identifier85053018460
dc.identifier000444527000092
dc.identifier.citationZhang , 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.8b02423en
dc.identifier.issn1523-7060
dc.identifier.otherORCID: /0000-0002-2104-7313/work/47928965
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861415
dc.identifier.urihttps://hdl.handle.net/10023/18368
dc.descriptionJET 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.abstractCatalytic 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.format.extent1220602
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleIsothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid : two-step synthesis of stereodefined dihydroindolizinonesen
dc.typeJournal articleen
dc.contributor.sponsorThe Leverhulme Trusten
dc.contributor.sponsorThe Royal Societyen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1021/acs.orglett.8b02423
dc.description.statusPeer revieweden
dc.date.embargoedUntil2019-08-24
dc.identifier.urlhttps://pubs.acs.org/doi/suppl/10.1021/acs.orglett.8b02423en
dc.identifier.grantnumberECF-2014-005en
dc.identifier.grantnumberWM140071en


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