Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons

Holmstedt, Suvi; George, Lijo; Koivuporras, Alisa; Valkonen, Arto; Candeias, Nuno R.

doi:10.1021/acs.orglett.0c02995

dc.contributor.author	Holmstedt, Suvi
dc.contributor.author	George, Lijo
dc.contributor.author	Koivuporras, Alisa
dc.contributor.author	Valkonen, Arto
dc.contributor.author	Candeias, Nuno R.
dc.date.accessioned	2021-02-01T11:24:12Z
dc.date.available	2021-02-01T11:24:12Z
dc.date.issued	2020
dc.identifier.citation	Holmstedt, S., George, L., Koivuporras, A., Valkonen, A., & Candeias, N. R. (2020). Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons. <i>Organic Letters</i>, <i>22</i>(21), 8370-8375. <a href="https://doi.org/10.1021/acs.orglett.0c02995" target="_blank">https://doi.org/10.1021/acs.orglett.0c02995</a>
dc.identifier.other	CONVID_42346865
dc.identifier.uri	https://jyx.jyu.fi/handle/123456789/73916
dc.description.abstract	The installation of vicinal mesylate and silyl ether groups in a quinic acid derivative generates a system prone for stereoselective borane-catalyzed hydrosilylation through a siloxonium intermediate. The diversification of the reaction conditions allowed the construction of different defunctionalized fragments foreseen as useful synthetic fragments. The selectivity of the hydrosilylation was rationalized on the basis of deuteration experiments and computational studies.	en
dc.format.mimetype	application/pdf
dc.language	eng
dc.language.iso	eng
dc.publisher	American Chemical Society (ACS)
dc.relation.ispartofseries	Organic Letters
dc.rights	In Copyright
dc.subject.other	redox reactions
dc.subject.other	reaction products
dc.subject.other	bond cleavage
dc.subject.other	ethers
dc.subject.other	hydrosilylation
dc.title	Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons
dc.type	research article
dc.identifier.urn	URN:NBN:fi:jyu-202102011373
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	8370-8375
dc.relation.issn	1523-7060
dc.relation.numberinseries	21
dc.relation.volume	22
dc.type.version	acceptedVersion
dc.rights.copyright	© 2020 American Chemical Society
dc.rights.accesslevel	openAccess	fi
dc.type.publication	article
dc.relation.grantnumber	314343
dc.subject.yso	hapetus-pelkistysreaktio
dc.subject.yso	eetterit
dc.subject.yso	orgaaniset yhdisteet
dc.subject.yso	kemiallinen synteesi
dc.format.content	fulltext
jyx.subject.uri	http://www.yso.fi/onto/yso/p28877
jyx.subject.uri	http://www.yso.fi/onto/yso/p3840
jyx.subject.uri	http://www.yso.fi/onto/yso/p3841
jyx.subject.uri	http://www.yso.fi/onto/yso/p8468
dc.rights.url	http://rightsstatements.org/page/InC/1.0/?language=en
dc.relation.doi	10.1021/acs.orglett.0c02995
dc.relation.funder	Research Council of Finland	en
dc.relation.funder	Suomen Akatemia	fi
jyx.fundingprogram	Research costs of Academy Research Fellow, AoF	en
jyx.fundingprogram	Akatemiatutkijan tutkimuskulut, SA	fi
jyx.fundinginformation	The Academy of Finland is duly acknowledged for financial support to N.R.C. (Decisions No. 326487 and 326486) and to A. V. (No. 314343). Finnish Cultural Foundation is acknowledged for financial support to S.H. (00190336).
dc.type.okm	A1

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