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

journal contribution
posted on 2023-05-19, 13:55 authored by Rivinoja, DJ, Gee, YS, Michael GardinerMichael Gardiner, Ryan, JH, Hyland, CJT
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.

History

Publication title

ACS Catalysis

Volume

7

Pagination

1053-1056

ISSN

2155-5435

Department/School

School of Natural Sciences

Publisher

AMER CHEMICAL SOC

Place of publication

1155 16TH ST, NW, WASHINGTON, DC 20036

Rights statement

© 2016 American Chemical Society

Repository Status

  • Restricted

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Expanding knowledge in the chemical sciences

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