University Of Tasmania
Browse

File(s) under permanent embargo

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

journal contribution
posted on 2023-05-19, 13:54 authored by Gee, YS, Rivinoja, DJ, Wales, SM, Michael GardinerMichael Gardiner, Ryan, JH, Hyland, CJT
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.

History

Publication title

Journal of Organic Chemistry

Volume

82

Issue

24

Pagination

13517-13529

ISSN

0022-3263

Department/School

School of Natural Sciences

Publisher

Amer Chemical Soc

Place of publication

1155 16Th St, Nw, Washington, USA, Dc, 20036

Rights statement

© 2017 American Chemical Society

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

Usage metrics

    University Of Tasmania

    Exports