Journal
TETRAHEDRON LETTERS
Volume 46, Issue 37, Pages 6305-6309Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.07.049
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A series of trialkylsilyl esters were deprotected or transesterificated into their corresponding carboxylic acids or methyl esters under a catalytic amount of CBr4 in alcohol reaction system. This method enables to desilylate secondary sp(3)-carbon, sp(2)-carbon, sp-carbon and aryl tethered trialkylsilyl esters to carboxylic acids, whereas primary sp(3)-carbon tethered trialkylsilyl esters were further converted into their methyl esters under CBr4/MeOH reaction conditions. The highly chemoselective deprotections can be modulated and achieved by the introduced protecting trialkylsilyl groups and the used alcohols such as MeOH and EtOH under this photochemically-induced reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.
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