Mild and Selective Deprotection of tert-Butyl(dimethyl)silyl Ethers with Catalytic­ Amounts of Sodium Tetrachloroaurate(III) Dihydrate

Qi Zhang*, Xiuqin Kang, Lei Long, Lijuan Zhu, Yonghai Chai*

*Shaanxi Normal University, 199 South Chang'an Road, Xi'an 710062, P. R. of China, Email: qiqizhangsnnu.edu.cn, ychaisnnu.edu.cn

Q. Zhang, X. Kang, L. Long, L. Zhu, Y. Chai, Synthesis, 2015, 47, 55-64.

DOI: 10.1055/s-0034-1379032

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Abstract

Sodium tetrachloroaurate(III) dihydrate as catalyst enables a simple and mild removal of tert-butyl(dimethyl)silyl (TBS) protecting groups. A selective deprotection of aliphatic TBS ethers is possible in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into benzyl ethers in one pot.

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Key Words

deprotection of tert-butyl(dimethyl)silyl ethers, alcohols, catalysis, gold

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ID: J66-Y2015