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Pd-catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates
Citation
Gee, YS and Rivinoja, DJ and Wales, SM and Gardiner, MG and Ryan, JH and Hyland, CJT, Pd-catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates, Journal of Organic Chemistry, 82, (24) pp. 13517-13529. ISSN 0022-3263 (2017) [Refereed Article]
Copyright Statement
© 2017 American Chemical Society
DOI: doi:10.1021/acs.joc.7b02624
Abstract
A trans-diastereoselective Pd-catalyzed dearomative [3 + 2] cycloaddition between vinylcyclopropane dicarboxylates and 3-nitroindoles has been developed. The reaction provides densely functionalized cyclopenta[b]indolines with versatile vinyl and nitro-groups. The addition of a halide additive was found to be critical for the diastereoselectivity of the reaction, which is proposed to be a result of a rapid π-σ-π interconversion between the intermediates allowing for Curtin–Hammett control. A switch in diastereoselectivity to afford products with the vinyl and nitro groups cis to each other is observed with a 4-substituted 3-nitroindole.
Item Details
| Item Type: | Refereed Article |
|---|---|
| Keywords: | Pd-catalyzed Dearomative |
| 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: | 122781 |
| Year Published: | 2017 |
| Web of Science® Times Cited: | 61 |
| Deposited By: | Chemistry |
| Deposited On: | 2017-11-28 |
| Last Modified: | 2022-08-22 |
| Downloads: | 0 |
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