Enantioselective synthesis of cyclic, quaternary oxonitriles

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dc.authoridhttps://orcid.org/0000-0002-3967-8404en_US
dc.contributor.authorGüneş, Yakup
dc.contributor.authorPolat, Muhammed Fatih
dc.contributor.authorŞahin, Ertan
dc.contributor.authorFleming, Fraser F.
dc.contributor.authorAltundaş, Ramazan
dc.date.accessioned2019-12-23T06:58:34Z
dc.date.available2019-12-23T06:58:34Z
dc.date.issued2010en_US
dc.departmentEğitim Fakültesien_US
dc.description.abstractQuaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition-elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while selectively forming a new quaternary center with enantiomeric ratios typically greater than 9:1. The overall alkylation strategy addresses the challenge of enantioselectively generating hindered, quaternary centers while simultaneously installing ketone, nitrile, and olefin functionalities.en_US
dc.description.sponsorshipTUBITAK (106T100)en_US
dc.identifier.citationGüneş, Y., Polat, M. F., Sahin, E., Fleming, F. F., & Altundas, R. (2010). Enantioselective synthesis of cyclic, quaternary oxonitriles. The Journal of organic chemistry, 75(21), 7092-7098.en_US
dc.identifier.doi10.1021/jo1011202
dc.identifier.endpage7098en_US
dc.identifier.issue21en_US
dc.identifier.startpage7092en_US
dc.identifier.urihttps://pubs.acs.org/doi/10.1021/jo1011202
dc.identifier.urihttps://hdl.handle.net/20.500.12604/2347
dc.identifier.volume75en_US
dc.institutionauthorGüneş, Yakup
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofThe Journal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası - Editör Denetimli Dergien_US
dc.rightsinfo:eu-repo/semantics/embargoedAccessen_US
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/us/*
dc.snmz#KayıtKontrol#
dc.subjectQuaternary Oxonitrilesen_US
dc.subjectEnantioselective Synthesisen_US
dc.titleEnantioselective synthesis of cyclic, quaternary oxonitrilesen_US
dc.typeArticleen_US

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