The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles

Daniel J. Rivinoja, Yi Sing Gee, Michael G. Gardiner, John H. Ryan, Christopher J.T. Hyland

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53 Citations (Scopus)

Abstract

An efficient, diastereoselective synthesis of densely functionalized pyrroloindolines is reported. The reaction proceeds via cycloaddition of a vinylaziridine-derived Pd-stabilized 1,3-dipole to electron-deficient 3-nitroindoles. The reactions give the trans diastereoisomer with high selectivity; however, when a 4-substituent is present on the indole ring, a reversal of diastereoselectivity is observed.

Original languageEnglish
Pages (from-to)1053-1056
Number of pages4
JournalACS Catalysis
Volume7
Issue number2
DOIs
Publication statusPublished - 3 Feb 2017
Externally publishedYes

Keywords

  • dearomatization
  • indoles
  • palladium catalysis
  • pyrroloindolines
  • vinylaziridines
  • [3 + 2] cycloaddition

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