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Palladium-Catalyzed Decarboxylative Formal (4 + 2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles

Journal Article


Abstract


  • A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H-indolo[2,3-b ]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.

Publication Date


  • 2020

Citation


  • Bird, M. J., Wales, S. M., Richardson, C., & Hyland, C. J. T. (2020). Palladium-Catalyzed Decarboxylative Formal (4 + 2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles. Synlett, 31(9), 916-924. doi:10.1055/s-0040-1707995

Scopus Eid


  • 2-s2.0-85085289125

Start Page


  • 916

End Page


  • 924

Volume


  • 31

Issue


  • 9

Abstract


  • A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H-indolo[2,3-b ]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.

Publication Date


  • 2020

Citation


  • Bird, M. J., Wales, S. M., Richardson, C., & Hyland, C. J. T. (2020). Palladium-Catalyzed Decarboxylative Formal (4 + 2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles. Synlett, 31(9), 916-924. doi:10.1055/s-0040-1707995

Scopus Eid


  • 2-s2.0-85085289125

Start Page


  • 916

End Page


  • 924

Volume


  • 31

Issue


  • 9