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Pd-catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates
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Gee, YS, Rivinoja, DJ, Wales, SM, Gardiner, MG
ORCID: 0000-0001-6373-4253, Ryan, JH and Hyland, CJT 2017
, 'Pd-catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates'
, Journal of Organic Chemistry, vol. 82, no. 24
, pp. 13517-13529
, doi: 10.1021/acs.joc.7b02624.

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Official URL: http://pubs.acs.org/doi/pdf/10.1021/acs.joc.7b0262...
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 Type: | Article |
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Authors/Creators: | Gee, YS and Rivinoja, DJ and Wales, SM and Gardiner, MG and Ryan, JH and Hyland, CJT |
Keywords: | Pd-catalyzed Dearomative |
Journal or Publication Title: | Journal of Organic Chemistry |
Publisher: | Amer Chemical Soc |
ISSN: | 0022-3263 |
DOI / ID Number: | 10.1021/acs.joc.7b02624 |
Copyright Information: | © 2017 American Chemical Society |
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