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Silver-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Ynol Ethers

Jing Yin, Yihui Bai, Mengyi Mao and Gangguo Zhu*

*Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China, Email: gangguozjnu.cn

J. Yin, Y. Bai, M. Mao, G. Zhu, J. Org. Chem., 2014, 79, 9179-9185.

DOI: 10.1021/jo501615a (free Supporting Information)



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Abstract

A silver-catalyzed trans addition of carboxylic acids to ynol ethers delivers a broad range of (Z)-α-alkoxy enol esters in good yields with excellent regio- and stereoselectivity. A subsequent Ni-catalyzed selective coupling of alkenyl C-OPiv bonds of (Z)-α-alkoxy enol esters with boronic acids enables a convenient route to (E)-enol ethers.


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Key Words

enols


ID: J42-Y2014