Desilylation procedure via a naphthalene-catalysed lithiation reaction |
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Authors: | Cherif Behloul |
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Affiliation: | Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain |
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Abstract: | The reaction of silyl protected alcohols, amines and thiols with lithium powder and a catalytic amount of naphthalene, in THF, at 0 °C led, after hydrolysis, to the recovery of the free alcohols, amines and thiols in very good yields. At least a phenyl group was required in the silyl protecting group for the success of the reaction. Some polyfunctionalised starting materials have successfully been deprotected. The stereochemical outcome of the deprotection of a silylated chiral secondary alcohol has also been studied and no racemization was observed. The process has shown to be a good alternative to the acid-catalysed desilylation procedures, the latter being not useful for the deprotection of some silylated tertiary alcohols. |
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Keywords: | Lithium Naphthalene Silyl Deprotection Desilylation Alcohols Amines Thiols |
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