Copper-Catalyzed Asymmetric Allyl Addition of Imines with Allenylsilanes

A copper-catalyzed allylation of N-<i>tert</i>-butanesulfinyl imines with silylallenes has been developed, affording chiral homoallylic amines bearing multiple stereocenters with excellent stereocontrol. The protocol features mild conditions, broad substrate scope, and robustness on a gram scale. Importantly, the allylsilane motif provides a versatile handle for downstream derivatizations. This strategy offers a practical and stereoselective approach to valuable homoallylic amines, highlighting its potential utility in asymmetric synthesis.

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Publication Details

Journal
Organic Letters
Published
2025-12-04
DOI
https://doi.org/10.1021/acs.orglett.5c04532
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
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article

Copper-Catalyzed Asymmetric Allyl Addition of Imines with Allenylsilanes

Shang Gao, Aijun Lin, Menghua Xu, Zhenhua Gu et al.
Organic Letters
Asymmetric Synthesis and Catalysis
article

Copper-Catalyzed Asymmetric Allyl Addition of Imines with Allenylsilanes

Shang Gao, Aijun Lin, Menghua Xu, Zhenhua Gu, Hui Miao, Peng Sun, Chi Yang
article en

Abstract

A copper-catalyzed allylation of N-<i>tert</i>-butanesulfinyl imines with silylallenes has been developed, affording chiral homoallylic amines bearing multiple stereocenters with excellent stereocontrol. The protocol features mild conditions, broad substrate scope, and robustness on a gram scale. Importantly, the allylsilane motif provides a versatile handle for downstream derivatizations. This strategy offers a practical and stereoselective approach to valuable homoallylic amines, highlighting its potential utility in asymmetric synthesis.

Organic LettersVol. 27(50)
Fuyang Normal University (CN), China Pharmaceutical University (CN), Chinese Academy of Medical Sciences & Peking Union Medical College (CN), China Academy of Chinese Medical Sciences (CN), Ministry of Industry and Information Technology (CN)
Openalex Percentile: Top 71%
Asymmetric Synthesis and Catalysis
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