Specific Z-Selectivity in the Oxidative Isomerization of Allyl Ethers to Generate Geometrically Defined Z-Enol Ethers Using a Cobalt(II)(salen) Complex Catalyst

Guanxin Huang, Miaolin Ke, Yuan Tao and Fener Chen*

*Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, P. R. China, Email: rfchenfudan.edu.cn

G. Huang, M. Ke, Y. Tao, F. Chen, J. Org. Chem., 2020, 85, 5321-5329.

DOI: 10.1021/acs.joc.0c00004

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Abstract

An efficient Z-selective oxidative isomerization process of allyl ethers catalyzed by a cobalt(II) (salen) complex using N-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate (Me₃NFPY•OTf) as an oxidant provides thermodynamically less stable Z-enol ethers in excellent yields with high geometric control. Diallyl ethers can also be isomerized at room temperature.

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Key Words

enol ethers, isomerization, allyl ethers, N-fluoro-2,4,6-trimethylpyridinium triflate

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ID: J42-Y2020