ArticleNature2011
Catalytic Z-selective olefin cross-metathesis for natural product synthesis.
Article in Nature, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 77 papers.
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Who cites it
77 citing papers in PubMed, 399 citations in OpenAlex.
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- Synthesis of Highly Substituted Alkenes from Terminal Alkynes.Journal of the American Chemical Society · 2025Article
- Synthesis of Azide-Labeled β-Lactosylceramide Analogs Containing Different Lipid Chains as Useful Glycosphingolipid Probes.Molecules (Basel, Switzerland) · 2025Article
- The stereo-divergent functionalization of alkynes: a comprehensive review.RSC advances · 2025Review
- Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping.Nature communications · 2024Article
- Accessing Z-Enynes via Cobalt-Catalyzed Propargylic Dehydrogenation.Angewandte Chemie (International ed. in English) · 2024Article
- Mechanism ofJournal of the American Chemical Society · 2024Article
- Stereoselective Copper-Catalyzed Olefination of Imines.Angewandte Chemie (International ed. in English) · 2024Article
- Asymmetric total synthesis strategies of halichlorine and pinnaic acid.RSC advances · 2023Review
- 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
- Stereoselective Synthesis of Trisubstituted Alkenes via Copper Hydride-Catalyzed Alkyne Hydroalkylation.Journal of the American Chemical Society · 2023Article
- Chromium-catalyzed stereodivergent E- and Z-selective alkyne hydrogenation controlled by cyclic (alkyl)(amino)carbene ligands.Nature communications · 2023Article
- Enantio- andScience advances · 2023Article
- Mechanistic dichotomy in the solvent dependent access toChemical science · 2022Article
- Enantioselective Organocopper-Catalyzed Hetero Diels-Alder Reaction throughJournal of the American Chemical Society · 2022Article
- Synthesis of medicinally relevant oxalylamines via copper/Lewis acid synergistic catalysis.Science advances · 2021Article
- Air-stable 18-electron adducts of Schrock catalysts with tuned stability constants for spontaneous release of the active species.Communications chemistry · 2021Article
- Selective E to Z isomerization of 1,3-Dienes Enabled by A Dinuclear Mechanism.Nature communications · 2021Article
- Olefin metathesis: what have we learned about homogeneous and heterogeneous catalysts from surface organometallic chemistry?Chemical science · 2021Review
17 more citing papers are in PubMed but not listed here.
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
Alkenes are found in many biologically active molecules, and there are a large number of chemical transformations in which alkenes act as the reactants or products (or both) of the reaction. Many alkenes exist as either the E or the higher-energy Z stereoisomer. Catalytic procedures for the stereoselective formation of alkenes are valuable, yet methods enabling the synthesis of 1,2-disubstituted Z alkenes are scarce. Here we report catalytic Z-selective cross-metathesis reactions of terminal enol ethers, which have not been reported previously, and of allylic amides, used until now only in E-selective processes. The corresponding disubstituted alkenes are formed in up to >98% Z selectivity and 97% yield. These transformations, promoted by catalysts that contain the highly abundant and inexpensive metal molybdenum, are amenable to gram-scale operations. Use of reduced pressure is introduced as a simple and effective strategy for achieving high stereoselectivity. The utility of this method is demonstrated by its use in syntheses of an anti-oxidant plasmalogen phospholipid, found in electrically active tissues and implicated in Alzheimer's disease, and the potent immunostimulant KRN7000.
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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.