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Chromium(III)-Catalyzed Addition of Water and Alcohol to α,β-Unsaturated Ketones for the Synthesis of β-Hydroxyl and β-Alkoxyl Ketones in Aqueous Media

Jin-Jin Yun, Xuan-Yu Liu, Wei Deng, Xue-Qiang Chu, Zhi-Liang Shen*, Teck-Peng Loh*

*Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China, Email: ias_zlshennjtech.edu.cn, teckpengntu.edu.sg

J.-J. Yun, X.-Y. Liu, W. Deng, X.-Q. Chu, Z.-L. Shen, T.-P. Loh, J. Org. Chem., 2018, 83, 10898-10907.

DOI: 10.1021/acs.joc.8b01584 (free Supporting Information)


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Abstract

A variety of α,β-unsaturated ketones effectively reacted in an efficient chromium(III) chloride-catalyzed Michael-type addition with either water or alcohols to give the corresponding β-hydroxyl ketones or β-alkoxyl ketones in good yields with excellent functional group compatibility. The approach was further utilized for the preparation of synthetically useful tetrahydrofuran derivatives.

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Key Words

hydroxylation


ID: J42-Y2018