Affiliation:
1. Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada.
Abstract
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 multifunctional substrates, including those bearing Cbz groups.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
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