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2019 (English)In: Nature Communications, 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.
National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-173116 (URN)10.1038/s41467-019-11838-x (DOI)000482398900028 ()31444355 (PubMedID)
2019-10-042019-10-042023-03-28Bibliographically approved