A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst

被引：27
|
作者：
Bothwell, Jason M. [1 ]
Angeles, Veronica V. [1 ]
Carolan, James P. [1 ]
Olson, Margaret E. [1 ]
Mohan, Ram S. [1 ]
机构：
[1] Dept Chem, Lab Environm Friendly Organ Synth, Bloomington, IL 61701 USA
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 07期
基金：
美国国家科学基金会;
关键词：
HIGHLY SELECTIVE DEPROTECTION; SILYL ETHERS; EFFICIENT METHOD; TETRAHYDROPYRANYL THP; CLEAVAGE; ACETALS; FACILE; SILICA; TBS; ACETONITRILE;
D O I：
10.1016/j.tetlet.2009.12.076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+F- (TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection of TBDMS, TES, and TIPS ethers using iron(III) tosylate as a catalyst. Phenolic TBDMS ethers, TBDPS ethers and the BOC group are not affected under these conditions. Iron(III) tosylate is an inexpensive, commercially available, and non-corrosive reagent. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1056 / 1058
页数：3
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