The Use of Tin (IV) Chloride to Selectively Cleave Benzyl Esters over Benzyl Ethers and Benzyl Amines
Baker, Alexander E. G.
Lund, Kate-lyn A.R.
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Benzyl esters are cleaved upon reaction with SnCl4, resulting in isolation of the corresponding carboxylic acid. Importantly, benzyl ethers, amines and amides do not undergo debenzylation under these conditions, nor do a variety of other common protecting groups for alcohols, thereby rendering SnCl4 selective amongst Lewis acids. The scope, tolerance and limitations of the strategy are demonstrated through the analysis of several multi-functional substrates, including those bearing Cbz groups.
Baker, A. E., Marchal, E., Lund, K. L. A., & Thompson, A. (2014). The use of tin (IV) chloride to selectively cleave benzyl esters over benzyl ethers and benzyl amines. Canadian Journal of Chemistry, 92(12), 1175-1185. https://doi.org/10.1139/cjc-2014-0364