Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation

被引：53

作者：

Ikawa, T ^{[1
]}

Hattori, K ^{[1
]}

Sajiki, H ^{[1
]}

Hirota, K ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Med Chem Lab, Gifu 5028585, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 32期

关键词：

silyl ether; hydrogenation; palladium on carbon; solvent effect; deprotection;

D O I：

10.1016/j.tet.2004.05.098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and dimethyl acetal under hydrogenation condition using 10% Pd/C in MeOH. In contrast, chemoselective hydrogenation of reducible functional groups such as acetylene, olefin and benzyl ether, proceeds in the presence of TBDMS or TES ethers in AcOEt or MeCN. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6901 / 6911

页数：11

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