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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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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
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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