Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


see article for more reactions

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.

see article for more examples



Key Words

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


ID: J66-Y2015