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dc.contributor.authorColgan, Avene C
dc.contributor.authorProctor, Rupert
dc.contributor.authorGibson, David C
dc.contributor.authorChuentragool, Padon
dc.contributor.authorLahdenperä, Antti SK
dc.contributor.authorErmanis, Kristaps
dc.contributor.authorPhipps, Robert
dc.date.accessioned2022-04-28T08:00:19Z
dc.date.available2022-04-28T08:00:19Z
dc.date.issued2022-06-20
dc.date.submitted2022-01-06
dc.identifier.issn1433-7851
dc.identifier.otheranie202200266
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/336540
dc.description.abstractCatalytic enantioselective Minisci reactions have recently been developed but all instances so far utilize α-amino radical coupling partners. We report a substantial evolution of the enantioselective Minisci reaction that enables α-hydroxy radicals to be used, providing valuable enantioenriched secondary alcohol products. This is achieved through the direct oxidative coupling of two C-H bonds on simple alcohol and pyridine partners through a hydrogen atom transfer (HAT)-driven approach: a challenging process to achieve due to the numerous side reactions that can occur. Our approach is highly regioselective as well as highly enantioselective. Dicumyl peroxide, upon irradiation with 390 nm light, serves as both HAT reagent and oxidant whilst selectivity is controlled by use of a chiral phosphoric acid catalyst. Computational and experimental evidence provide mechanistic insight as to the origin of selectivity, revealing a stereodetermining deprotonation step distinct from the analogous reaction of amide-containing substrates.
dc.languageen
dc.publisherWiley
dc.subjectResearch Article
dc.subjectResearch Articles
dc.subjectAsymmetric Catalysis
dc.subjectChiral Phosphoric Acids
dc.subjectHeterocycles
dc.subjectMinisci Reaction
dc.subjectOrganocatalysis
dc.titleHydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols.
dc.typeArticle
dc.date.updated2022-04-28T08:00:18Z
prism.publicationNameAngew Chem Int Ed Engl
dc.identifier.doi10.17863/CAM.83960
dcterms.dateAccepted2022-04-14
rioxxterms.versionofrecord10.1002/anie.202200266
rioxxterms.versionAO
rioxxterms.versionVoR
rioxxterms.licenseref.urihttp://creativecommons.org/licenses/by/4.0/
dc.contributor.orcidProctor, Rupert [0000-0002-2296-448X]
dc.contributor.orcidErmanis, Kristaps [0000-0001-9703-8758]
dc.contributor.orcidPhipps, Robert [0000-0002-7383-5469]
dc.identifier.eissn1521-3773
pubs.funder-project-idEuropean Research Council (757381)
pubs.funder-project-idEngineering and Physical Sciences Research Council (1918560)
pubs.funder-project-idEngineering and Physical Sciences Research Council (EP/S03269X/1)
pubs.funder-project-idRoyal Society (URF\R\191003)
pubs.funder-project-idEPSRC (1943646)
pubs.funder-project-idEPSRC (1800778)
pubs.funder-project-idEngineering and Physical Sciences Research Council (EP/P020259/1)
cam.issuedOnline2022-04-27


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