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dc.contributor.authorProctor, Ruperten
dc.contributor.authorDavis, Holly Jen
dc.contributor.authorPhipps, Roberten
dc.date.accessioned2018-05-15T14:27:02Z
dc.date.available2018-05-15T14:27:02Z
dc.date.issued2018-04-05en
dc.identifier.issn0036-8075
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/275816
dc.description.abstractBasic heteroarenes are a ubiquitous feature of pharmaceuticals and bioactive molecules, and Minisci-type additions of radical nucleophiles are a leading method for their elaboration. Despite many Minisci-type protocols that result in the formation of stereocenters, exerting control over the absolute stereochemistry at these centers remains an unmet challenge. We report a process for addition of prochiral radicals, generated from amino acid derivatives, to pyridines and quinolines with excellent control of both enantioselectivity and regioselectivity. An enantiopure chiral Brønsted acid catalyst serves both to activate the substrate and induce asymmetry, while an iridium photocatalyst mediates the required electron transfer processes. We anticipate that this method will expedite access to enantioenriched small-molecule building blocks bearing versatile basic heterocycles.
dc.format.mediumPrint-Electronicen
dc.languageengen
dc.titleCatalytic enantioselective Minisci-type addition to heteroarenes.en
dc.typeArticle
prism.endingPage422
prism.issueIdentifier6387en
prism.publicationDate2018en
prism.publicationNameScience (New York, N.Y.)en
prism.startingPage419
prism.volume360en
dc.identifier.doi10.17863/CAM.23083
dcterms.dateAccepted2018-02-28en
rioxxterms.versionofrecord10.1126/science.aar6376en
rioxxterms.versionAM*
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/all-rights-reserveden
rioxxterms.licenseref.startdate2018-04-05en
dc.contributor.orcidProctor, Rupert [0000-0002-2296-448X]
dc.contributor.orcidDavis, Holly J [0000-0003-3968-9311]
dc.contributor.orcidPhipps, Robert [0000-0002-7383-5469]
dc.identifier.eissn1095-9203
rioxxterms.typeJournal Article/Reviewen
pubs.funder-project-idEPSRC (EP/N005422/1)
pubs.funder-project-idRoyal Society (uf130004)
pubs.funder-project-idEPSRC (1918560)
rioxxterms.freetoread.startdate2018-10-05


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