Asymmetric Synthesis of Chiral Diamines via a Low-Loading Ir-Catalyzed Umpolung Allylation of Imines

A general and mild method for the synthesis of homoallylic 1,2-diamines from α-amino aldimines is reported. This method capitalizes on a low-loading iridium-catalyzed asymmetric umpolung allylation of imines and the following facile 2-aza-Cope rearrangement. The reagents are derived from readily available starting materials, and the catalytic system enables efficient construction of chiral vicinal diamines under mild conditions with broad functional group tolerance.

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Journal
Organic Letters
Published
2025-07-19
DOI
https://doi.org/10.1021/acs.orglett.5c02466
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Asymmetric Synthesis of Chiral Diamines via a Low-Loading Ir-Catalyzed Umpolung Allylation of Imines

Dawen Niu, Rong Shi, Hongbao Sun, Yingwei Wang
1 links
Organic Letters
Asymmetric Hydrogenation and Catalysis
article

Asymmetric Synthesis of Chiral Diamines via a Low-Loading Ir-Catalyzed Umpolung Allylation of Imines

Dawen Niu, Rong Shi, Hongbao Sun, Yingwei Wang
article en

Abstract

A general and mild method for the synthesis of homoallylic 1,2-diamines from α-amino aldimines is reported. This method capitalizes on a low-loading iridium-catalyzed asymmetric umpolung allylation of imines and the following facile 2-aza-Cope rearrangement. The reagents are derived from readily available starting materials, and the catalytic system enables efficient construction of chiral vicinal diamines under mild conditions with broad functional group tolerance.

Organic LettersVol. 27(30)
Sichuan University (CN), West China Hospital of Sichuan University (CN)
Nuclear Power Institute of China, National Natural Science Foundation of China, Sichuan University, Sichuan Province Science and Technology Support Program
Openalex Percentile: Top 86%
Asymmetric Hydrogenation and Catalysis
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