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Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0003-0203-8478
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 92019 (English)In: Nature Communications, ISSN 2041-1723, E-ISSN 2041-1723, Vol. 10, article id 3826Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2019. Vol. 10, article id 3826
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Chemical Sciences
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URN: urn:nbn:se:su:diva-173116DOI: 10.1038/s41467-019-11838-xISI: 000482398900028PubMedID: 31444355OAI: oai:DiVA.org:su-173116DiVA, id: diva2:1357532
Available from: 2019-10-04 Created: 2019-10-04 Last updated: 2019-10-04Bibliographically approved

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Watile, Rahul A.Bunrit, AnonMargalef, JèssicaAkkarasamiyo, SunisaAyub, RabiaRepo, TimoSamec, Joseph S. M.
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