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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: yusua.es

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

DOI: 10.1016/S0040-4039(97)01328-2


Abstract

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.

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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