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Updated: Mar 14, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Catalytic Asymmetric Umpolung Allylation of Imines
Jie Liu1, Chao-Guo Cao1, Hong-Bao Sun1
1Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan University, and Collaborative Innovation Center for Biotherapy , Chengdu 610041, China.
Abstract:
Here we report an iridium-catalyzed asymmetric umpolung allylation of imines as a general approach to prepare 1,4-disubstituted homoallylic amines, a fundamental class of compounds that are hitherto not straightforward to obtain. This transformation proceeds by a cascade involving an intermolecular regioselective allylation of 2-azaallyl anions and a following 2-aza-Cope rearrangement, utilizes easily available reagents and catalysts, tolerates a substantial scope of substrates, and readily leads to various enantioenriched, 1,4-disubstituted homoallylic primary amines.
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