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Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction

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dc.creator TANYELİ, CİHANGİR
dc.creator Cayir, Merve
dc.creator Demirci, Sema
dc.creator Sezer, Serdar
dc.date 2011-06-14T21:00:00Z
dc.date.accessioned 2020-10-06T11:24:08Z
dc.date.available 2020-10-06T11:24:08Z
dc.identifier cebba67d-eb3b-4f82-8805-45a04b28944e
dc.identifier 10.1016/j.tetasy.2011.07.003
dc.identifier https://avesis.sdu.edu.tr/publication/details/cebba67d-eb3b-4f82-8805-45a04b28944e/oai
dc.identifier.uri http://acikerisim.sdu.edu.tr/xmlui/handle/123456789/72461
dc.description A ring closing metathesis reaction of dienes and a ring closing enyne metathesis reaction derived from allyl, homoallyl and homopropargyl alcohol backbones are described. 2-Heteroaryl substituted allyl, homoallyl and homopropargyl alcohols have been easily and efficiently resolved through enzymatic resolution with high ee (93-99%) and known stereochemistry. Enantiomerically enriched dienes derived from allyl and homoallyl alcohols afforded the corresponding enantiomerically enriched dihydrofuran and dihydropyran derivatives, respectively, with chemical yields which varied between 72% and 88%. On the other hand, enantiomerically enriched enynes derived from homoallyl and homopropargyl alcohols gave the corresponding optically active dihydropyrans with conjugated diene units with chemical yields between 70% and 80%. A subsequent Diels-Alder reaction of the dihydropyran derivatives with a diene unit with tetracyanoethylene resulted in the formation of a diastereomeric dihydroisochromene ring system as the sole product. (C) 2011 Elsevier Ltd. All rights reserved.
dc.language eng
dc.rights info:eu-repo/semantics/closedAccess
dc.title Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction
dc.type info:eu-repo/semantics/article


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