Chemoenzymatic route to various spirocyclic compounds based on enantiomerically enriched tertiary allylic, homoallylic, and homopropargylic alcohols

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dc.authorid0000-0003-2270-8635en_US
dc.authorid0000-0002-8828-0507
dc.contributor.authorTanyeli, Cihangir
dc.contributor.authorÖzdemirhan, Devrim
dc.date.accessioned2021-06-23T19:36:03Z
dc.date.available2021-06-23T19:36:03Z
dc.date.issued2014
dc.departmentBAİBÜ, Fen Edebiyat Fakültesi, Kimya Bölümüen_US
dc.description.abstractA ring closing metathesis (RCM) reaction of dienes and an intramolecular Pauson-Khand (PKR) reaction of enynes derived from tertiary allyl, homoallyl, and homopropargyl alcohol backbones to afford the corresponding spirocyclic dihydrofuran and dihydropyrans and spirocyclic cyclopentenone pyrans, respectively, are described. Cyclopent-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols la-c have been efficiently resolved via enzymatic resolution with high ee (up to 90%) with 44%, 40%, and 43% chemical yields, respectively. Moreover, the cyclohex-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols 3a-c have also been resolved in the same manner with high ee (up to 97%) and in 42%, 45%, and 49% chemical yields. Enantiomerically enriched dienes derived from tertiary homoallyl alcohols yield the corresponding enantiomerically enriched spirocyclic dihydropyran derivatives via RCM with 74% and 78% chemical yields and with 90% and 97% ee, respectively. Moreover, enantiomerically enriched enynes derived from tertiary homoallyl alcohols afford the corresponding enantiomerically enriched cyclopentenone pyrans with spirocyclic motifs via PKR with 80% and 81% chemical yields, respectively, and as single diastereomers. (C) 2014 Elsevier Ltd. All rights reserved.en_US
dc.identifier.doi10.1016/j.tetasy.2014.03.004
dc.identifier.endpage666en_US
dc.identifier.issn0957-4166
dc.identifier.issue8en_US
dc.identifier.scopus2-s2.0-84899934077en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.startpage658en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2014.03.004
dc.identifier.urihttps://hdl.handle.net/20.500.12491/7919
dc.identifier.volume25en_US
dc.identifier.wosWOS:000336708800011en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.institutionauthorÖzdemirhan, Devrim
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron-Asymmetryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.titleChemoenzymatic route to various spirocyclic compounds based on enantiomerically enriched tertiary allylic, homoallylic, and homopropargylic alcoholsen_US
dc.typeArticleen_US

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