Deacylation of Esters, Thioesters and Amides by a Naphthalene-Catalysed Lithiation

Cherif Behloul, David Guijarro, Miguel Yus*

*Instituto de Síntesis Orgánica (ISO) and Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain, Email: yusua.es

C. Behloul, D. Guijarro, M. Yus, Synthesis, 2006, 309-314.

DOI: 10.1055/s-2005-918501

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Abstract

The reaction of different esters, thioesters and amides derived from pivalic, benzoic and 4-tert-butylbenzoic acids with an excess of lithium and a catalytic amount of naphthalene led, after methanolysis, to the corresponding alcohols, thiols and amines, respectively, through a reductive non-hydrolytic procedure.

see article for more examples

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Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation

E. Alonso, D. J. Ramón, M. Yus, Tetrahedron, 1997, 53, 14355-14368.

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Key Words

deacylation (esters, thioesters, amides), pivalates, benzoates, lithium

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ID: J66-Y2006-290