ArticleAngewandte Chemie (International ed. in English)2017
Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- The Catalytic Enantioselective Sommelet-Hauser Rearrangement.Journal of the American Chemical Society · 2026Article
- Unprecedented Copper/Iron-Cocatalyzed Homocoupling of Propargyl Ethers to Conjugated Benzofurans.JACS Au · 2025Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- A highly diastereoselective strain-release Doyle-Kirmse reaction: access to functionalized difluoro(methylene)cyclopropanes.Chemical science · 2023Article
- Recent advances in metal-catalysed asymmetric sigmatropic rearrangements.Chemical science · 2022Review
- Catalytic rearrangements of onium ylides in aromatic systems.Organic & biomolecular chemistry · 2022Review
- Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides.Journal of the American Chemical Society · 2021Article
- Rhodium-catalyzed cascade reactions of triazoles with organoselenium compounds - a combined experimental and mechanistic study.Chemical science · 2021Article
- Recent Perspectives on Rearrangement Reactions of Ylides via Carbene Transfer Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.Trends in chemistry · 2020Article
- Ring Expansion of Bicyclic Methyleneaziridines via Concerted, Near-Barrierless [2,3]-Stevens Rearrangements of Aziridinium Ylides.ACS catalysis · 2018Article
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2 authors.
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Abstract
The first highly enantioselective, diastereoselective, and regioselective [2,3]-rearrangement of iodonium ylides has been developed as a general solution to catalytic onium ylide rearrangements. In the presence of a chiral copper catalyst, substituted allylic iodides couple with α-diazoesters to generate metal-coordinated iodonium ylides, which undergo [2,3]-rearrangements with high selectivities (up to >95:5 r.r., up to >95:5 d.r., and up to 97 % ee). The enantioenriched iodoester products can be converted stereospecifically into a variety of onium ylide rearrangement products, as well as compounds that are not accessible by classical onium ylide rearrangements.
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