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Aminative Umpolung of Aldehydes to α-Amino Anion Equivalents for Pd-Catalyzed Allylation: An Efficient Synthesis of Homoallylic Amines

Lei Ding, Jing Chen, Yifan Hu, Juan Xu, Xing Gong, Dongfang Xu, Baoguo Zhao* and Hexing Li

*The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Lab of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234, China, Email: zhaobg2006shnu.edu.cn

L. Ding, J. Chen, Y. Hu, J. Xu, X. Gong, D. Xu, B. Zhao, H. Li, Org. Lett., 2014, 16, 720-723.

DOI: 10.1021/ol4034012 (free Supporting Information)



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Abstract

Aromatic aldehydes can be converted to α-amino anion equivalents via amination with 2,2-diphenylglycine and subsequent decarboxylation. These in situ generated α-imino anions are highly reactive for Pd-catalyzed allylation to give homoallylic amines in high yields with excellent regioselectivity.

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Key Words

homoallylic amines, benzylic amines


ID: J54-Y2014