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

页码：1056 / 1058

页数：3

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