eCite Digital Repository

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

Citation

Gee, YS and Rivinoja, DJ and Wales, SM and Gardiner, MG and Ryan, JH and Hyland, CJT, Pd-catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates, Journal of Organic Chemistry, 82, (24) pp. 13517-13529. ISSN 0022-3263 (2017) [Refereed Article]

Copyright Statement

© 2017 American Chemical Society

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

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 Details

Item Type:Refereed Article
Keywords:Pd-catalyzed Dearomative
Research Division:Chemical Sciences
Research Group:Inorganic Chemistry
Research Field:Transition Metal Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Gardiner, MG (Associate Professor Michael Gardiner)
ID Code:122781
Year Published:2017
Web of Science® Times Cited:11
Deposited By:Chemistry
Deposited On:2017-11-28
Last Modified:2018-04-27
Downloads:0

Repository Staff Only: item control page