Journal article

Synthesis of Medium-Sized Carbocycles via a Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels-Alder Reaction Followed by Photoinduced Ring-Opening


Authors listRuhl, J; Ahles, S; Strauss, MA; Leonhardt, CM; Wegner, HA

Publication year2021

Pages2089-2093

JournalOrganic Letters

Volume number23

Issue number6

ISSN1523-7060

eISSN1523-7052

DOI Linkhttps://doi.org/10.1021/acs.orglett.1c00249

PublisherAmerican Chemical Society


Abstract
The combination of a Lewis acid-catalyzed inverse electron-demand Diels-Alder (IEDDA) reaction with a photoinduced ring-opening (PIRO) reaction in a domino process has been established as an efficient synthetic method to access medium-sized carbocycles. From readily available electron-rich and electron-poor phthalazines and enamines, respectively, as starting materials, various 9- and 11-membered carbocycles were prepared. This versatile transition-metal-free tool will be valuable for broadening the structural space in biologically active compounds and functional materials.



Citation Styles

Harvard Citation styleRuhl, J., Ahles, S., Strauss, M., Leonhardt, C. and Wegner, H. (2021) Synthesis of Medium-Sized Carbocycles via a Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels-Alder Reaction Followed by Photoinduced Ring-Opening, Organic Letters, 23(6), pp. 2089-2093. https://doi.org/10.1021/acs.orglett.1c00249

APA Citation styleRuhl, J., Ahles, S., Strauss, M., Leonhardt, C., & Wegner, H. (2021). Synthesis of Medium-Sized Carbocycles via a Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels-Alder Reaction Followed by Photoinduced Ring-Opening. Organic Letters. 23(6), 2089-2093. https://doi.org/10.1021/acs.orglett.1c00249


Last updated on 2025-21-05 at 16:47