ArticleNature communications2019
Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron(III) catalyst.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- The catalytic enantioselective [1,2]-Wittig rearrangement cascade of allylic ethers.Nature chemistry · 2026Article
- Scalable reductive deuteration of (Hetero)Aryl chlorides with DNature communications · 2025Article
- Formally Stereoretentive SJournal of the American Chemical Society · 2025Article
- A New Insight into the Molecular Mechanism of the Reaction between 2-Methoxyfuran and Ethyl (Molecules (Basel, Switzerland) · 2024Article
- Recent Advances in Metal-Catalyzed Approaches for the Synthesis of Quinazoline Derivatives.Molecules (Basel, Switzerland) · 2024Review
- Deoxyfluorination of 1°, 2°, and 3° Alcohols by Nonbasic O-H Activation and Lewis Acid-Catalyzed Fluoride Shuttling.Journal of the American Chemical Society · 2023Article
- Highly Diastereoselective Preparation of Tertiary Alkyl Isonitriles by Stereoinvertive Nucleophilic Substitution at a Nonclassical Carbocation.Organic letters · 2023Article
- Enantioselective Synthesis of Atropisomers by Oxidative Aromatization with Central-to-Axial Conversion of Chirality.Molecules (Basel, Switzerland) · 2023Review
- Chemical insights into the synthetic chemistry of five-membered saturated heterocycles-a transition metal-catalyzed approach.Frontiers in chemistry · 2023Review
- Transition-metal-catalyzed synthesis of quinazolines: A review.Frontiers in chemistry · 2023Review
- Photoredox-catalyzed C-C bond cleavage of cyclopropanes for the formation of C(spNature communications · 2022Article
- Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers.Angewandte Chemie (International ed. in English) · 2022Article
- Benzyl thioether formation merging copper catalysis.RSC advances · 2021Article
- Organophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides.Nature communications · 2021Article
- Hydrogen-bond donor and acceptor cooperative catalysis strategy for cyclic dehydration of diols to access O-heterocycles.Science advances · 2021Article
- Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres.Chemical science · 2020Review
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Authors and funding
9 authors.
Funding
No grant is acknowledged in the PubMed record.
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.
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Registered trials
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