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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

Description

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
URI: http://hdl.handle.net/1885/209305
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/c9ob01363f

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