Metal-Free Method for Direct Synthesis of Functionalized β-Ketoenamines

Xiaobao Zeng, Chulong Liu, Weiguang Yang, Yunxiang Weng, Xinyan Wang*, Yuefei Hu*

*Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China, Email: wangxinyanmail.tsinghua.edu.cn, yfhmail.tsinghua.edu.cn

X. Zeng, C. Liu, W. Yang, Y. Weng, X. Wang, Y. Hu, J. Org. Chem., 2019, 84, 3656-3661.

DOI: 10.1021/acs.joc.8b03247

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Abstract

A BF₃·OEt₂-catalyzed cyclization of 1-iodoalkyne and α-keto acid followed by an amine-mediated ring-opening enable a metal-free direct synthesis of β-ketoenamines in one pot. The reaction tolerates transition metal-sensitive functional groups.

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proposed mechanism

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Key Words

Enaminones (C=C, C-N)

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ID: J42-Y2019