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The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles
Citation
Rivinoja, DJ and Gee, YS and Gardiner, MG and Ryan, JH and Hyland, CJT, The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles, ACS Catalysis, 7, (2) pp. 1053-1056. ISSN 2155-5435 (2017) [Refereed Article]
Copyright Statement
© 2016 American Chemical Society
DOI: doi:10.1021/acscatal.6b03248
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.
Item Details
| Item Type: | Refereed Article |
|---|---|
| Keywords: | pyrroloindolines, palladium catalysis, dearomatization, indoles, [3 + 2] cycloaddition, vinylaziridines |
| Research Division: | Chemical Sciences |
| Research Group: | Inorganic Chemistry |
| Research Field: | Transition Metal Chemistry |
| Objective Division: | Expanding Knowledge |
| Objective Group: | Expanding Knowledge |
| Objective Field: | Expanding Knowledge in the Chemical Sciences |
| UTAS Author: | Gardiner, MG (Associate Professor Michael Gardiner) |
| ID Code: | 122792 |
| Year Published: | 2017 |
| Web of Science® Times Cited: | 34 |
| Deposited By: | Chemistry |
| Deposited On: | 2017-11-29 |
| Last Modified: | 2018-03-29 |
| Downloads: | 0 |
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