Skip navigation
Skip navigation

1,2-Addition versus homoconjugate addition reactions of indoles and electron-rich arenes to alpha-cyclopropyl N-acyliminium ions: synthetic and computational studies

Ryder, Gregory; Wille, Uta; Willis, Anthony; Pyne, Stephen G


An investigation of the reactivity of α-cyclopropyl N-acyliminium ions towards indoles has resulted in the unprecedented synthesis of 5-cyclopropyl-5-(3-indoyl)pyrrolidin-2-ones via 1,2-addition reactions and, in the case of highly electron deficient indoles and electron rich arenes, spiroheterocycles via sequential homoconjugate and 1,2-addition reactions with often high diastereoselective control at the C-5 quaternary stereocentres. Computational studies provided support for the proposed...[Show more]

CollectionsANU Research Publications
Date published: 2019
Type: Journal article
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/c9ob01363f


File Description SizeFormat Image
01_Ryder_1%2C2-Addition_versus_2019.pdf1.52 MBAdobe PDF    Request a copy

Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.

Updated:  19 May 2020/ Responsible Officer:  University Librarian/ Page Contact:  Library Systems & Web Coordinator