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

Rahul A. Watile, Anon Bunrit, Jèssica Margalef, Sunisa Akkarasamiyo, Rabia Ayub, Emi Lagerspets, Srijit Biswas, Timo Repo () and Joseph S. M. Samec ()
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Rahul A. Watile: Stockholm University
Anon Bunrit: Stockholm University
Jèssica Margalef: Stockholm University
Sunisa Akkarasamiyo: Stockholm University
Rabia Ayub: Stockholm University
Emi Lagerspets: University of Helsinki
Srijit Biswas: University of Calcutta
Timo Repo: University of Helsinki
Joseph S. M. Samec: Stockholm University

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-019-11838-x

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