ArticleAngewandte Chemie (International ed. in English)2016
Dirhodium(II)-Catalyzed Annulation of Enoldiazoacetamides with α-Diazoketones: An Efficient and Highly Selective Approach to Fused and Bridged Ring Systems.
Article in Angewandte Chemie (International ed. in English), 2016. 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.
- Two Distinct Diazo-Diazo Cross-Coupling Reactions between α-Aryldiazo Ketones and Vinyldiazo Esters Using Gold Catalyst and Tetrabutylammonium Fluoride.Organic letters · 2025Article
- Structure-property relationships of photofunctional diiridium(II) complexes with tetracationic charge and an unsupported Ir-Ir bond.Communications chemistry · 2022Article
- Enantioselective (8+3) Cycloadditions by Activation of Donor-Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Challenges in the Highly Selective [3 + 1]-Cycloaddition of an Enoldiazoacetamide to Form a Donor-AcceptorMolecules (Basel, Switzerland) · 2021Article
- Asymmetric synthesis of dihydro-1,3-dioxepines by Rh(ii)/Sm(iii) relay catalytic three-component tandem [4 + 3]-cycloaddition.Chemical science · 2021Article
- Formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloaddition reactions of donor-acceptor cyclobutenes, cyclopropenes and siloxyalkynes induced by Brønsted acid catalysis.Chemical science · 2021Article
- Regio- and Diastereoselective Dimerization of Diazo Carbonyls: A Cooperative Catalytic Approach to Complex Scaffolds with Four Contiguous Stereocenters.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.Organic & biomolecular chemistry · 2019Review
- Copper-Catalyzed Formal [4+2] Cycloaddition of Enoldiazoimides with Sulfur Ylides.Angewandte Chemie (International ed. in English) · 2018Article
- Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds.Angewandte Chemie (International ed. in English) · 2017Article
- Cycloaddition reactions of enoldiazo compounds.Chemical Society reviews · 2017Review
- Functionalizing the γ-Position of α-Diazo-β-ketoesters.Tetrahedron letters · 2016Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
A dirhodium(II)-catalyzed annulation reaction between two structurally different diazocarbonyl compounds furnishes the donor-acceptor cyclopropane-fused benzoxa[3.2.1]octane scaffold with excellent chemo-, regio-, and diastereoselectivity under exceptionally mild conditions. The composite transformation occurs by [3+2]-cycloaddition between donor-acceptor cyclopropenes generated from enoldiazoacetamides and carbonyl ylides formed from intramolecular carbene-carbonyl cyclization in one pot with one catalyst. The annulation products can be readily transformed into benzoxa[3.3.1]nonane and hexahydronaphthofuran derivatives with exact stereocontrol. This method allows the efficient construction of three fused and bridged ring systems, all of which are important skeletons of numerous biologically active natural products.
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Registered trials
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