Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones
| dc.contributor.author | Csókás, Dániel | |
| dc.contributor.author | Siitonen, Juha H. | |
| dc.contributor.author | Pihko, Petri M. | |
| dc.contributor.author | Pápai, Imre | |
| dc.date.accessioned | 2020-06-25T07:50:48Z | |
| dc.date.available | 2020-06-25T07:50:48Z | |
| dc.date.issued | 2020 | |
| dc.identifier.citation | Csókás, 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.other | CONVID_35322810 | |
| dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/70921 | |
| dc.description.abstract | A 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.mimetype | application/pdf | |
| dc.language | eng | |
| dc.language.iso | eng | |
| dc.publisher | American Chemical Society | |
| dc.relation.ispartofseries | Organic Letters | |
| dc.rights | CC BY 4.0 | |
| dc.subject.other | chemical structure | |
| dc.subject.other | enolates | |
| dc.subject.other | transition states | |
| dc.subject.other | selectivity | |
| dc.subject.other | organic reactions | |
| dc.title | Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones | |
| dc.type | article | |
| dc.identifier.urn | URN:NBN:fi:jyu-202006255110 | |
| dc.contributor.laitos | Kemian laitos | fi |
| dc.contributor.laitos | Department of Chemistry | en |
| dc.contributor.oppiaine | Orgaaninen kemia | fi |
| dc.contributor.oppiaine | Organic 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 | 4597-4601 | |
| dc.relation.issn | 1523-7060 | |
| dc.relation.numberinseries | 12 | |
| dc.relation.volume | 22 | |
| dc.type.version | publishedVersion | |
| dc.rights.copyright | © 2020 American Chemical Society | |
| dc.rights.accesslevel | openAccess | fi |
| dc.subject.yso | kemialliset reaktiot | |
| dc.subject.yso | orgaaniset yhdisteet | |
| dc.subject.yso | isomeria | |
| dc.subject.yso | alkaloidit | |
| dc.format.content | fulltext | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p3658 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p3841 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p10129 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p11306 | |
| dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
| dc.relation.doi | 10.1021/acs.orglett.0c01008 | |
| jyx.fundinginformation | Financial 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. | |
| dc.type.okm | A1 |
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