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

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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

Title: Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst
Author: Watile, Rahul A.; Bunrit, Anon; Margalef, Jessica; Akkarasamiyo, Sunisa; Ayub, Rabia; Lagerspets, Emi; Biswas, Srijit; Repo, Timo; Samec, Joseph S. M.
Contributor: University of Helsinki, Department
University of Helsinki, Department of Chemistry
Date: 2019-08-23
Language: eng
Number of pages: 9
Belongs to series: Nature Communications
ISSN: 2041-1723
URI: http://hdl.handle.net/10138/305562
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.
Subject: ALLYLIC ALCOHOLS
NUCLEOPHILIC-SUBSTITUTION
ALKYLATION
MECHANISMS
AMINATION
SOLVOLYSES
EFFICIENCY
AMINES
116 Chemical sciences
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