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Regioselective and Stereoselective Entry to β,β-Disubstituted Vinyl Ethers via the Sequential Hydroboration/Suzuki-Miyaura Coupling of Ynol Ethers

Weijian Cui, Mengyi Mao, Zuying He and Gangguo Zhu*

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

W. Cui, M. Mao, Z. He, G. Zhu, J. Org. Chem., 2013, 78, 9815-9821.

DOI: 10.1021/jo401523m (free Supporting Information)


Abstract

A sequential hydroboration/Suzuki-Miyaura coupling of ynol ethers allows a highly regio- and stereoselective synthesis of stereodefined β,β-disubstituted alkenyl ethers. A number of functional groups are well-tolerated under the reaction conditions. Furthermore, the reaction enables a facile entry to labile diarylacetaldehydes by TFA-mediated hydrolysis of the β,β-disubstituted vinyl ethers.

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Key Words

hydroboration, Suzuki Coupling, α-arylation, olefination, hydrolysis


ID: J42-Y2013