The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles

Authors

Daniel Rivinoja, University of WollongongFollow
Yi Sing Gee, University of WollongongFollow
Michael G. Gardiner, University of Tasmania
Jack Ryan, CSIRO Manufacturing FlagshipFollow
Christopher J. T Hyland, University of WollongongFollow

RIS ID

111849

Publication Details

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 1053-1056.

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.