Diastereoselective Control Through Hydrogen Bonding in the Aziridination of the Chiral Allylic Alcohols by Acetoxyaminoquinazolinone

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dc.authoridCakici, Murat/0000-0002-7020-0302
dc.authoridKarabuga, semistan/0000-0001-9753-206X
dc.contributor.authorCakici, Murat
dc.contributor.authorKarabuga, Semistan
dc.contributor.authorKilic, Hamdullah
dc.contributor.authorUlukanli, Sabri
dc.contributor.authorSahin, Ertan
dc.contributor.authorSevin, Fatma
dc.date.accessioned2025-08-12T08:25:04Z
dc.date.issued2009
dc.departmentOsmaniye Korkut Ata Üniversitesi
dc.description.abstractA high diastereoselectivity (up to > 99:1) is found for the aziridinations of chiral allylic alcohols with acetoxyaminoquinazolinone (Q-NHOAc). The selectivity is explained in terms of hydrogen bonding between the hydroxy functionality of the allylic alcohol and the remote carbonyl group of the quinazolinone.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [TBAG-108T116]
dc.description.sponsorshipFinancial support by the Scientific and Technological Research Council of Turkey (TUBITAK) (TBAG-108T116) is gratefully acknowledged. In addition the authors would like to thank Dr. Graham Eaton from Leicester University for HRMS measurements. M.C. would like to thank TUBITAK for a scholarship.
dc.identifier.doi10.1021/jo902092s
dc.identifier.endpage9459
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.issue24
dc.identifier.pmid19916513
dc.identifier.scopusqualityQ2
dc.identifier.startpage9452
dc.identifier.urihttps://doi.org/10.1021/jo902092s
dc.identifier.urihttps://hdl.handle.net/20.500.12502/4700
dc.identifier.volume74
dc.identifier.wosWOS:000272462100027
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250812
dc.subjectTransition-State Geometry
dc.subjectCatalytic Epoxidation
dc.subjectGroup Directivity
dc.subjectMediated Aziridination
dc.subjectAlkenes
dc.subject3-Acetoxyaminoquinazolinones
dc.subjectStrain
dc.subjectAgents
dc.subjectAcid
dc.subject(Z)-3-Methyl-3-Penten-2-Ol
dc.titleDiastereoselective Control Through Hydrogen Bonding in the Aziridination of the Chiral Allylic Alcohols by Acetoxyaminoquinazolinone
dc.typeArticle

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