Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst

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dc.contributor University of Helsinki, Department en
dc.contributor University of Helsinki, Department of Chemistry en
dc.contributor.author Watile, Rahul A.
dc.contributor.author Bunrit, Anon
dc.contributor.author Margalef, Jessica
dc.contributor.author Akkarasamiyo, Sunisa
dc.contributor.author Ayub, Rabia
dc.contributor.author Lagerspets, Emi
dc.contributor.author Biswas, Srijit
dc.contributor.author Repo, Timo
dc.contributor.author Samec, Joseph S. M.
dc.date.accessioned 2019-09-23T11:14:01Z
dc.date.available 2019-09-23T11:14:01Z
dc.date.issued 2019-08-23
dc.identifier.citation Watile , R A , Bunrit , A , Margalef , J , Akkarasamiyo , S , Ayub , R , Lagerspets , E , Biswas , S , Repo , T & Samec , J S M 2019 , ' Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst ' , Nature Communications , vol. 10 , 3826 . https://doi.org/10.1038/s41467-019-11838-x en
dc.identifier.issn 2041-1723
dc.identifier.other PURE: 126937696
dc.identifier.other PURE UUID: 83be22c9-02b7-4cf0-8dea-52c6e3d876bd
dc.identifier.other WOS: 000482398900028
dc.identifier.other ORCID: /0000-0002-3116-6199/work/62276903
dc.identifier.other ORCID: /0000-0003-2338-8389/work/62280508
dc.identifier.uri http://hdl.handle.net/10138/305562
dc.description.abstract Optically pure alcohols are abundant in nature and attractive as feedstock for organic synthesis but challenging for further transformation using atom efficient and sustainable methodologies, particularly when there is a desire to conserve the chirality. Usually, substitution of the OH group of stereogenic alcohols with conservation of chirality requires derivatization as part of a complex, stoichiometric procedure. We herein demonstrate that a simple, inexpensive, and environmentally benign iron(III) catalyst promotes the direct intramolecular substitution of enantiomerically enriched secondary and tertiary alcohols with O-, N-, and S-centered nucleophiles to generate valuable 5-membered, 6-membered and aryl-fused 6-membered heterocyclic compounds with chirality transfer and water as the only byproduct. The power of the methodology is demonstrated in the total synthesis of (+)-lentiginosine from D-glucose where iron-catalysis is used in a key step. Adoption of this methodology will contribute towards the transition to sustainable and bio-based processes in the pharmaceutical and agrochemical industries. en
dc.format.extent 9
dc.language.iso eng
dc.relation.ispartof Nature Communications
dc.rights en
dc.subject ALLYLIC ALCOHOLS en
dc.subject NUCLEOPHILIC-SUBSTITUTION en
dc.subject ALKYLATION en
dc.subject MECHANISMS en
dc.subject AMINATION en
dc.subject SOLVOLYSES en
dc.subject EFFICIENCY en
dc.subject AMINES en
dc.subject 116 Chemical sciences en
dc.title Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst en
dc.type Article
dc.description.version Peer reviewed
dc.identifier.doi https://doi.org/10.1038/s41467-019-11838-x
dc.type.uri info:eu-repo/semantics/other
dc.type.uri info:eu-repo/semantics/publishedVersion
dc.contributor.pbl
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