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Zinc-Mediated Highly α-Regioselective Prenylation of Imines with Prenyl Bromide

Li-Ming Zhao*, Shu-Qing Zhang, Hai-Shan Jin, Li-Jing Wan and Fei Dou

*Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou 221116, Jiangsu, China, Email:

L.-M. Zhao, S.-Q. Zhang, H.-S. Jin, L.-J. Wan, F. Dou, Org. Lett., 2012, 14, 886-889.

DOI: 10.1021/ol203410m

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A highly α-regioselective prenylation of imines enables the conversion a wide range of substrates including N- and C-aryl aldimines, N-alkyl aldimines, C-alkyl aldimines, and N- and C-aryl ketimines. The approach uses prenyl bromide as prenyl source and inexpensive zinc as mediator as well as environmentally benign 1,3-dimethyl-2-imidazolidinone (DMI) as solvent.

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Key Words

Homoallylamines, Zinc

ID: J54-Y2012-0340