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

doi:10.1021/acs.joc.7b02624

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

Journal article

Peer reviewed

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 and Christopher J. T Hyland

Journal of Organic Chemistry, Vol.82(24), pp.13517-13529

2017

DOI: https://doi.org/10.1021/acs.joc.7b02624

PMID: 29129063

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Abstract

addition reactions

cyclization

indoles

molecular structure

steroselectivity

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.

Details

Title: Pd-Catalyzed Dearomative [3 + 2] Cycloaddition of 3‑Nitroindoles with 2‑Vinylcyclopropane-1,1-dicarboxylates
Authors: Yi Sing Gee (Author) - University of Wollongong
Daniel J Rivinoja (Author) - University of Wollongong
Steven M Wales (Author) - University of Wollongong
Michael G Gardiner (Author) - University of Tasmania
John H Ryan (Author) - CSIRO Manufacturing
Christopher J. T Hyland (Corresponding Author) - University of Wollongong
Publication details: Journal of Organic Chemistry, Vol.82(24), pp.13517-13529
Publisher: American Chemical Society
DOI: 10.1021/acs.joc.7b02624
ISSN: 1520-6904
PMID: 29129063
Organisation Unit: Student Services and Engagement; School of Science, Technology and Engineering
Language: English
Record Identifier: 99707484702621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Organic

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