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

Emma Alonso, Diego J. Ramón and Miguel Yus*

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain, Email:

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

DOI: 10.1016/S0040-4020(97)00920-4


The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective.

see article for more reactions

see article for more examples

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

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

Key Words

benzyl ethers, toluenesulfonamides, lithium

ID: J72-Y1997-680