Alkali-Amide-Catalyzed One-Pot Aminoallylation of Aldehydes with Allylbenzenes

Yuanyun Gu, Yan-En Wang, Yaqi Yuan, Haodong Xu, Yizhou Lu, Yufei Zhang, Fei Xue, Dan Xiong and Jianyou Mao*

*School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu 211816, P. R. China, Email: ias_jymaonjtech.edu.cn

Y. Gu, Y.-E. Wang, Y. Yuan, H. Xu, Y. Lu, Y. Zhang, F. Xue, D. Xiong, J. Mao, J. Org. Chem., 2023, 88, 7362-7372.

DOI: 10.1021/acs.joc.3c00581

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Abstract

(NaN(SiMe₃)₂) catalyzes a deprotonation of allylbenzenes. Trapping of the deprotonated allyl anion with in situ generated N-(trimethylsilyl) aldimines provides value-added homoallylic amines with excellent linear selectivity.

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proposed mechanism

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Key Words

primary amines (C-N), homoallylic amines (C-N), homoallylic amines (C-C), multicomponent reactions

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ID: J42-Y2023