Iodine-Mediated Oxidative Dehydrogenation of β-Acylamino Ketones for the Highly Stereoselective Synthesis of (Z)-β-Keto­enamides

Hong-Hong Chang, Fei Hu, Wen-Chao Gao*, Tao Liu, Xing Li, Wen-Long Wei, Yan Qiao*

*Taiyuan University of Technology, Taiyuan 030024; Chinese Academy of Sciences, Taiyuan 030001, P. R. of China, Email: gaowenchaotyut.edu.cn, qiaoysxicc.ac.cn

H.-H. Chang, F. Hu, W.-C. Gao, T. Liu, X. Li, W.-L. Wei, Y. Qiao, Synlett, 2016, 27, 1592-1596.

DOI: 10.1055/s-0035-1561582

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Abstract

An iodine-mediated oxidative dehydrogenation of β-acylamino ketones gives β-ketoenamides in moderate yields. Only Z-isomers are produced due to the intramolecular H-bonding interaction in the HI-elimination step.

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Key Words

molecular iodine, dehydrogenation, β-acylamino ketones, β-ketoenamides, Z-selectivity

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ID: J60-Y2016