A New Mild Deprotecting Method for O-Benzylsulfonyl Phenols and Alcohols Based on a DTBB-Catalyzed Lithiation

Francisco Alonso; Yanina Moglie; Cristian Vitale; Gabriel Radivoy; Miguel Yus

doi:10.1055/s-2005-869907

PAPER

A New Mild Deprotecting Method for O-Benzylsulfonyl Phenols and Alcohols Based on a DTBB-Catalyzed Lithiation

Francisco Alonso^a, Yanina Moglie^b, Cristian Vitale^b, Gabriel Radivoy*^b, Miguel Yus*^a
^a Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
Fax: +34(96)5903549; e-Mail: yus@ua.es;
^b Instituto de Investigaciones en Química Orgánica (INIQO), Departamento de Química, Universidad Nacional del Sur, Avda. Alem 1253, 8000 Bahía Blanca, Argentina
Fax: +54(291)4595187; e-Mail: gradivoy@criba.edu.ar;

Abstract

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Abstract

A variety of alcohols and phenols, protected as the corresponding benzylsulfonic esters, were efficiently deprotected by selective reductive cleavage of the sulfur-oxygen bond, using an excess of lithium sand and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB) as electron carrier, in THF at 0° C. This deprotection system was also efficient at -50 °C and was compatible with a wide range of other functional groups.

Key words

benzylsulfonyl - protecting group - alcohols - phenols - reductive deprotection

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