Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones

Csókás, Dániel; Siitonen, Juha H.; Pihko, Petri M.; Pápai, Imre

doi:10.1021/acs.orglett.0c01008

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	research 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.type.publication	article
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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Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones

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