Author, as appears in the article.: Scharnagel, Dagmar; Escofet, Imma; Armengol-Relats, Helena; Elena de Orbe, M.; Nepomuk Korber, J.; Echavarren, Antonio M.;

Department: Química Analítica i Química Orgànica

URV's Author/s: ECHAVARREN PABLOS, ANTONIO

Keywords: Total synthesis Intermolecular 2+2 cycloaddition Gold catalysis Cyclopropanation Constituents Alkynes Alkenes Acetylene gold catalysis cyclopropanation acetylene

Abstract: The gold(I)-catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)-1,4-disubstituted 1,3-butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user-friendly procedure. Reaction of acetylene with 1,5-dienes gives rise stereoselectively to tricyclo[5.1.0.0(2,4)]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.

Thematic Areas: Química Medicina ii Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Astronomia / física

licence for use: https://creativecommons.org/licenses/by/3.0/es/

ISSN: 1433-7851

Author's mail: antoniomaria.echavarren@urv.cat

Author identifier: 0000-0002-6418-7930

Record's date: 2022-07-23

Journal volume: 59

Papper version: info:eu-repo/semantics/publishedVersion

Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201915895

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

Papper original source: Angewandte Chemie (International Ed. Print). 59 (12): 4888-4891

APA: Scharnagel, Dagmar; Escofet, Imma; Armengol-Relats, Helena; Elena de Orbe, M.; Nepomuk Korber, J.; Echavarren, Antonio M.; (2020). Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step. Angewandte Chemie (International Ed. Print), 59(12), 4888-4891. DOI: 10.1002/anie.201915895

Article's DOI: 10.1002/anie.201915895

Entity: Universitat Rovira i Virgili

Journal publication year: 2020

Publication Type: Journal Publications