PAPER	Synthesis 2006: 309-314   DOI: 10.1055/s-2005-918501
© Georg Thieme Verlag Stuttgart · New York
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 Fax: +34(96)5903549; e-Mail: yus@ua.es;
Received 18 July 2005

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 (8 mol%) led, after methanolysis, to the corresponding alcohols, thiols and amines, respectively, through a reductive non-hydrolytic procedure. This methodology represents a reasonable alternative to other non-reductive protocols.

Key words

esters - thioesters - amides - deacylation - lithium