Catalytic Asymmetric Umpolung Allylation of Imines

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-10, Vol.138 (40), p.13103-13106
Main Authors: Liu, Jie, Cao, Chao-Guo, Sun, Hong-Bao, Zhang, Xia, Niu, Dawen
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b05288