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dc.contributor.authorCsókás, Dániel
dc.contributor.authorSiitonen, Juha H.
dc.contributor.authorPihko, Petri M.
dc.contributor.authorPápai, Imre
dc.date.accessioned2020-06-25T07:50:48Z
dc.date.available2020-06-25T07:50:48Z
dc.date.issued2020
dc.identifier.citationCsókás, D., Siitonen, J. H., Pihko, P. M., & Pápai, I. (2020). Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones. <i>Organic Letters</i>, <i>22</i>(12), 4597-4601. <a href="https://doi.org/10.1021/acs.orglett.0c01008" target="_blank">https://doi.org/10.1021/acs.orglett.0c01008</a>
dc.identifier.otherCONVID_35322810
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/70921
dc.description.abstractA stereoselectivity model inspired by the total synthesis of stemona alkaloids is developed to explain why enolate-derived 3,4-fused butyrolactones are methylated with a preference for syn alkylation. The model shows how conformational locking present in nonplanar enolate structures favors syn over anti methylation, due to less significant structural distortions in the syn pathway. The developed model was also successfully used to rationalize selectivities of previously documented methylation reactions.en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.ispartofseriesOrganic Letters
dc.rightsCC BY 4.0
dc.subject.otherchemical structure
dc.subject.otherenolates
dc.subject.othertransition states
dc.subject.otherselectivity
dc.subject.otherorganic reactions
dc.titleConformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202006255110
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.description.reviewstatuspeerReviewed
dc.format.pagerange4597-4601
dc.relation.issn1523-7060
dc.relation.numberinseries12
dc.relation.volume22
dc.type.versionpublishedVersion
dc.rights.copyright© 2020 American Chemical Society
dc.rights.accesslevelopenAccessfi
dc.subject.ysokemialliset reaktiot
dc.subject.ysoorgaaniset yhdisteet
dc.subject.ysoisomeria
dc.subject.ysoalkaloidit
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p3658
jyx.subject.urihttp://www.yso.fi/onto/yso/p3841
jyx.subject.urihttp://www.yso.fi/onto/yso/p10129
jyx.subject.urihttp://www.yso.fi/onto/yso/p11306
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.1021/acs.orglett.0c01008
jyx.fundinginformationFinancial support from the Academy of Finland (project #259532), Jenny and Artturi Wihuri Foundation (research grant to J.H.S.), University of Jyväskylä (postgraduate fellowship to J.H.S), and NKFIH Hungary (grant K-112028) is gratefully acknowledged.


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