ArticleJournal of the American Chemical Society2014
Preparation of macrocyclic Z-enoates and (E,Z)- or (Z,E)-dienoates through catalytic stereoselective ring-closing metathesis.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Biobased Cyclic Enoate Monomers: Enabling Intrinsically Crystalline, Chemically Recyclable, Ultratough Polymers.Angewandte Chemie (International ed. in English) · 2026Article
- Divergent access to E- or Z-trisubstituted medium-sized cycloalkenes by Pd-catalysed cycloaddition.Nature chemistry · 2025Article
- Unsaturated Macrolactones from Renewable Feedstocks: Synthesis, Ring-Opening Polymerization and Application Prospects.International journal of molecular sciences · 2025Review
- Merging Grubbs second-generation catalyst with photocatalysis enablesChemical science · 2022Article
- The Reaction of β,γ-Epoxy Alcohols with Titanium(III) Reagents. A Proposed Role for Intramolecular Hydrogen Bonding.Tetrahedron · 2019Article
- Mechanism of Olefin Metathesis with Neutral and Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes.Journal of the American Chemical Society · 2019Article
- A remote C-C bond cleavage-enabled skeletal reorganization: Access to medium-/large-sized cyclic alkenes.Science advances · 2017Article
- Syntheses of Molybdenum Adamantylimido andOrganometallics · 2017Article
- Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.Angewandte Chemie (International ed. in English) · 2016Article
- Article
- Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes.Journal of the American Chemical Society · 2015Article
- Exo-selective reductive macrocyclization of ynals.Organic letters · 2015Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The first examples of catalyst-controlled stereoselective macrocyclic ring-closing metathesis reactions that generate Z-enoates as well as (E,Z)- or (Z,E)-dienoates are disclosed. Reactions promoted by 3.0-10 mol % of a Mo-based monoaryloxide pyrrolide complex proceed to completion within 2-6 h at room temperature. The desired macrocycles are formed in 79:21 to >98:2 Z/E selectivity; stereoisomerically pure products can be obtained in 43-75% yield after chromatography. Utility is demonstrated by application to a concise formal synthesis of the natural product (+)-aspicilin.
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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.