Pd-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates

Yi Sing Gee, Daniel J. Rivinoja, Steven M. Wales, Michael G. Gardiner, John H. Ryan, Christopher J.T. Hyland*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

47 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)13517-13529
Number of pages13
JournalJournal of Organic Chemistry
Volume82
Issue number24
Early online date15 Dec 2017
DOIs
Publication statusPublished - 15 Dec 2017

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