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The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles
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Rivinoja, DJ, Gee, YS, Gardiner, MG 
ORCID: 0000-0001-6373-4253, Ryan, JH and Hyland, CJT 2017
, 'The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles'
, ACS Catalysis, vol. 7, no. 2
, pp. 1053-1056
, doi: 10.1021/acscatal.6b03248.
ORCID: 0000-0001-6373-4253, Ryan, JH and Hyland, CJT 2017
, 'The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles'
, ACS Catalysis, vol. 7, no. 2
, pp. 1053-1056
, doi: 10.1021/acscatal.6b03248.
Full text not available from this repository.
Official URL: https://pubs.acs.org/doi/pdf/10.1021/acscatal.6b03...
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 Type: | Article |
|---|---|
| Authors/Creators: | Rivinoja, DJ and Gee, YS and Gardiner, MG and Ryan, JH and Hyland, CJT |
| Keywords: | pyrroloindolines, palladium catalysis, dearomatization, indoles, [3 + 2] cycloaddition, vinylaziridines |
| Journal or Publication Title: | ACS Catalysis |
| Publisher: | AMER CHEMICAL SOC |
| ISSN: | 2155-5435 |
| DOI / ID Number: | 10.1021/acscatal.6b03248 |
| Copyright Information: | © 2016 American Chemical Society |
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| Item Statistics: | View statistics for this item |
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