ArticleNature2015
High-value alcohols and higher-oxidation-state compounds by catalytic Z-selective cross-metathesis.
Article in Nature, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
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Who cites it
41 citing papers in PubMed, 219 citations in OpenAlex.
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- Stereo-reversed E2 unlocksScience (New York, N.Y.) · 2025Article
- Synthesis of Highly Substituted Alkenes from Terminal Alkynes.Journal of the American Chemical Society · 2025Article
- Tungsten-catalyzed stereodivergent isomerization of terminal olefins.Chemical science · 2025Article
- Preserving precise choreography of bonds in Z-stereoretentive olefin metathesis by using quinoxaline-2,3-dithiolate ligand.Nature communications · 2024Article
- Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping.Nature communications · 2024Article
- Mechanism ofJournal of the American Chemical Society · 2024Article
- An Anthracene-Thiolate-Ligated Ruthenium Complex: Computational Insights into Z-Stereoselective Cross Metathesis.The journal of physical chemistry. A · 2023Article
- A tunable family of CAAC-ruthenium olefin metathesis catalysts modularly derived from a large-scale produced ibuprofen intermediate.Chemical science · 2023Article
- Organocatalyst-mediated, pot-economical total synthesis of latanoprost.Chemical science · 2023Article
- Unexpected Latency ofOrganometallics · 2023Article
- Article
- Mesomeric Acceleration Counters Slow Initiation of Ruthenium-CAAC Catalysts for Olefin Metathesis (CAAC = Cyclic (Alkyl)(Amino) Carbene).ACS catalysis · 2023Article
- Enantio- andScience advances · 2023Article
- Stereocontrolled acyclic diene metathesis polymerization.Nature chemistry · 2023Article
- Iron-Catalyzed Olefin Metathesis: Recent Theoretical and Experimental Advances.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress.Molecules (Basel, Switzerland) · 2022Review
- Fatty Acids and their Derivatives as Renewable Platform Molecules for the Chemical Industry.Angewandte Chemie (International ed. in English) · 2021Review
- Unprecedented Nonphotomediated Hole (ACS central science · 2021Article
- Cationic Group VI Metal Imido Alkylidene N-Heterocyclic Carbene Nitrile Complexes: Bench-Stable, Functional-Group-Tolerant Olefin Metathesis Catalysts.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Olefin metathesis catalysts provide access to molecules that are indispensable to physicians and researchers in the life sciences. A persisting problem, however, is the dearth of chemical transformations that directly generate acyclic Z allylic alcohols, including products that contain a hindered neighbouring substituent or reactive functional units such as a phenol, an aldehyde, or a carboxylic acid. Here we present an electronically modified ruthenium-disulfide catalyst that is effective in generating such high-value compounds by cross-metathesis. The ruthenium complex is prepared from a commercially available precursor and an easily generated air-stable zinc catechothiolate. Transformations typically proceed with 5.0 mole per cent of the complex and an inexpensive reaction partner in 4-8 hours under ambient conditions; products are obtained in up to 80 per cent yield and 98:2 Z:E diastereoselectivity. The use of this catalyst is demonstrated in the synthesis of the naturally occurring anti-tumour agent neopeltolide and in a single-step stereoselective gram-scale conversion of a renewable feedstock (oleic acid) to an anti-fungal agent. In this conversion, the new catalyst promotes cross-metathesis more efficiently than the commonly used dichloro-ruthenium complexes, indicating that its utility may extend beyond Z-selective processes.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.