Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution
| dc.contributor.author | Axelsson, Anton | |
| dc.contributor.author | Westerlund, Mathias | |
| dc.contributor.author | Zacharias, Savannah C. | |
| dc.contributor.author | Runemark, August | |
| dc.contributor.author | Haukka, Matti | |
| dc.contributor.author | Sundén, Henrik | |
| dc.date.accessioned | 2021-07-08T07:29:24Z | |
| dc.date.available | 2021-07-08T07:29:24Z | |
| dc.date.issued | 2021 | |
| dc.identifier.citation | Axelsson, A., Westerlund, M., Zacharias, S. C., Runemark, A., Haukka, M., & Sundén, H. (2021). Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution. <i>European Journal of Organic Chemistry</i>, <i>2021</i>(25), 3657-3661. <a href="https://doi.org/10.1002/ejoc.202100491" target="_blank">https://doi.org/10.1002/ejoc.202100491</a> | |
| dc.identifier.other | CONVID_98929885 | |
| dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/77054 | |
| dc.description.abstract | An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, with good-to-moderate yields. Mechanistic studies indicate that the rate-determining step of the reaction is the formation of the Breslow intermediate, while the selectivity determining step occurs later in the mechanism. The presented methodology enables rapid synthesis of complex structures in a single step. | en |
| dc.format.mimetype | application/pdf | |
| dc.language.iso | eng | |
| dc.publisher | Wiley | |
| dc.relation.ispartofseries | European Journal of Organic Chemistry | |
| dc.rights | CC BY 4.0 | |
| dc.title | Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution | |
| dc.type | research article | |
| dc.identifier.urn | URN:NBN:fi:jyu-202107084240 | |
| dc.contributor.laitos | Kemian laitos | fi |
| dc.contributor.laitos | Department of Chemistry | en |
| dc.contributor.oppiaine | Epäorgaaninen ja analyyttinen kemia | fi |
| dc.contributor.oppiaine | Epäorgaaninen kemia | fi |
| dc.contributor.oppiaine | Inorganic and Analytical Chemistry | en |
| dc.contributor.oppiaine | Inorganic Chemistry | en |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
| dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
| dc.description.reviewstatus | peerReviewed | |
| dc.format.pagerange | 3657-3661 | |
| dc.relation.issn | 1434-193X | |
| dc.relation.numberinseries | 25 | |
| dc.relation.volume | 2021 | |
| dc.type.version | publishedVersion | |
| dc.rights.copyright | © 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH | |
| dc.rights.accesslevel | openAccess | fi |
| dc.type.publication | article | |
| dc.subject.yso | synteesi | |
| dc.subject.yso | kemialliset reaktiot | |
| dc.subject.yso | kemiallinen synteesi | |
| dc.format.content | fulltext | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p8467 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p3658 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p8468 | |
| dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
| dc.relation.doi | 10.1002/ejoc.202100491 | |
| jyx.fundinginformation | Funding from the Swedish Research Council (VR 2014-04664 and Formas 2016-00484, 2019-00699) is gratefully acknowledged.S.C.Z. thanks Olle Engkvist Stiftelse and Å-forsk Foundation for thepostdoctoral fellowship funding | |
| dc.type.okm | A1 |
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