Highly Efficient Deacetylation by Use of the Neutral Organotin Catalyst [tBu2SnOH(Cl)]2

Abstract

Deprotection of acetyl esters is effected cleanly by the neutral organotin catalyst, [tBu2SnOH(Cl)]2. The mildness of the reaction gives rise to great synthetic versatility and in the process a variety of functional groups are tolerated. Differentiations between primary, secondary, and tertiary alcohols and between acetyl ester and other esters are feasible. No racemization occurs with chiral acetyl esters. Exclusive deprotection of primary acetyl esters in carbohydrates and nucleosides is observed. The crude product thus obtained can be used for further reactions without purification.