An Efficient Acylation of Tertiary Alcohols with Isopropenyl Acetate Mediated by an Oxime Ester and Cp(2)Sm(thf)(2).

Abstract

An efficient method for the acylation of tertiary alcohols with isopropenyl acetate (1) by the use of an oxime and Cp(2)Sm(thf)(2) as catalyst was developed. Thus, various types of tertiary alcohols could be acylated with 1 in the presence of a catalytic amount of cyclohexanone oxime acetate (2) and Cp(2)Sm(thf)(2) under mild conditions to form the corresponding acetates in excellent yields. Acid-sensitive terpene alcohols such as linalool were successfully acetylated by the present method to give acetyl linalool in quantitative yield. This method enables an alternative acylation of tertiary alcohols under acid-free conditions.