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Reductive Deprotection of Boc-Protected Alcohols, Amines and Thiols via a DTBB-Catalysed Lithiation Process
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1  Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

Abstract: The DTBB-catalysed lithiation of Boc-protected alcohols, amines and thiols in THF at 0ºC led, after quenching with methanol, to the recovery of the free alcohols, amines and thiols in short reaction times and with very good yields. The procedure has been applied to primary, secondary and tertiary alcohols, secondary amines and a primary thiol. This method represents a reasonable alternative to the previously reported deprotection procedures.
Keywords: lithium; DTBB; tert-butoxycarbonyl; Boc; deprotection; alcohols; amines; thiols