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Enantioselective Vinylogous Amination of 5-Alkyl-4-nitroisoxazoles with a Dipeptide-Based Guanidinium Phase-Transfer Catalyst

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dc.contributor.authorZhu, Bo
dc.contributor.authorLee, Richmond
dc.contributor.authorYin, Yanli
dc.contributor.authorLi, Fuyuan
dc.contributor.authorCoote, Michelle
dc.contributor.authorJiang, Zhiyong
dc.date.accessioned2020-08-31T03:27:37Z
dc.date.available2020-08-31T03:27:37Z
dc.date.issued2018-01-02
dc.description.abstractAn enantioselective vinylogous amination of 5-alkyl-4-nitroisoxazoles is reported. With a novel chiral dipeptide-based urea-amide-guanidinium as the phase-transfer catalyst, the reactions worked efficiently with NaOAc as the base, affording valuable and challenging-to-synthesize chiral isoxazole derivatives featuring a single stereocenter at the α-position in high yields and with excellent enantioselectivities. Theoretical studies with DFT predicted that cooperative multiple hydrogen-bonding and ion pairing interactions of a nucleophile and NaOAc with the catalyst is crucial to deprotonation by reducing their HOMO-LUMO energy gap.en_AU
dc.description.sponsorshipZ.J. acknowledges the grants from NSFC (21672052) and SNPPIT (BX201700071). R.L. acknowledges a Faculty Early Career Award from SUTD. M.L.C. acknowledges Australian Research Council funding (CE140100012).en_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn1523-7060en_AU
dc.identifier.urihttp://hdl.handle.net/1885/209139
dc.language.isoen_AUen_AU
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/7793..."The Accepted version can be archived in a Non-Commercial Institutional Repository if required by funder. 12 months embargo" from SHERPA/RoMEO site (as at 31/08/2020). This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.orglett.7b03759en_AU
dc.publisherAmerican Chemical Societyen_AU
dc.relationhttp://purl.org/au-research/grants/arc/CE140100012en_AU
dc.rights© 2018 American Chemical Societyen_AU
dc.sourceOrganic lettersen_AU
dc.titleEnantioselective Vinylogous Amination of 5-Alkyl-4-nitroisoxazoles with a Dipeptide-Based Guanidinium Phase-Transfer Catalysten_AU
dc.typeJournal articleen_AU
dcterms.accessRightsOpen Accessen_AU
local.bibliographicCitation.issue2en_AU
local.bibliographicCitation.lastpage432en_AU
local.bibliographicCitation.startpage429en_AU
local.contributor.affiliationLee, R., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationCoote, Michelle, Research School of Chemistry, The Australian National Universityen_AU
local.contributor.authoruidu4031074en_AU
local.identifier.citationvolume20en_AU
local.identifier.doi10.1021/acs.orglett.7b03759en_AU
local.identifier.essn1523-7052en_AU
local.publisher.urlhttp://pubs.acs.org/journal/orlef7/about.htmlen_AU
local.type.statusAccepted Versionen_AU

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