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

F. ALONSO; Y. MOGLIE; C. VITALE; G. RADIVOY; M. YUS

SYNTHESIS-STUTTGART

Georg Thieme

Año: 2005 p. 1971 - 1976

0039-7881

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 tetrahydrofuran at 0º C. This deprotection system was also efficient at –50 ºC and was compatible with a wide range of other functional groups.