Skip to main content
placeholder image

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

Journal Article


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.

UOW Authors


  •   Rivinoja, Daniel (external author)
  •   Gee, Yi Sing (external author)
  •   Gardiner, Michael G. (external author)
  •   Ryan, Jack H. (external author)
  •   Hyland, Christopher

Publication Date


  • 2017

Citation


  • Rivinoja, D. J., Gee, Y., Gardiner, M. G., Ryan, J. H. & Hyland, C. J. T. (2017). The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles. ACS Catalysis, 7 (2), 1053-1056.

Scopus Eid


  • 2-s2.0-85019040849

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/4298

Has Global Citation Frequency


Number Of Pages


  • 3

Start Page


  • 1053

End Page


  • 1056

Volume


  • 7

Issue


  • 2

Place Of Publication


  • United States

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.

UOW Authors


  •   Rivinoja, Daniel (external author)
  •   Gee, Yi Sing (external author)
  •   Gardiner, Michael G. (external author)
  •   Ryan, Jack H. (external author)
  •   Hyland, Christopher

Publication Date


  • 2017

Citation


  • Rivinoja, D. J., Gee, Y., Gardiner, M. G., Ryan, J. H. & Hyland, C. J. T. (2017). The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles. ACS Catalysis, 7 (2), 1053-1056.

Scopus Eid


  • 2-s2.0-85019040849

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/4298

Has Global Citation Frequency


Number Of Pages


  • 3

Start Page


  • 1053

End Page


  • 1056

Volume


  • 7

Issue


  • 2

Place Of Publication


  • United States