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Selective cleavage of 3,5-bis-(trifluoromethyl)benzylcarbamate by SmI2-Et3N-H2O

Journal article
Authors Tobias Ankner
Anna Said Stålsmeden
Göran Hilmersson
Published in Chemical Communications
Volume 49
Issue 61
Pages 6867-6869
ISSN 1359-7345
Publication year 2013
Published at Department of Chemistry and Molecular Biology
Pages 6867-6869
Language en
Links dx.doi.org/10.1039/c3cc41642a
Keywords amino-protecting group, samarium(ii) iodide, organic-chemistry, peptide-synthesis, reductions, additives, diiodosamarium, deprotection, alcohols, reagent
Subject categories Organic Chemistry

Abstract

A novel electron poor protection group for amines has been developed. It undergoes rapid cleavage by SmI2-Et3N-H2O and its orthogonality towards the regular benzyl carbamate group (CBz) under reductive or transfer hydrogenolytic conditions is reported.

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