A highly efficient, two-step synthesis of 2-(dimethylphenylsilyl)ethanol (DMPSE-OH) was developed via the Karstedt-catalyzed hydrosilylation of vinyl acetate followed by basic hydrolysis, providing the product in 76% overall yield. The utility of DMPSE-OH was demonstrated as a protecting group for carboxylic acids, including aromatic, aliphatic, and amino acid derivatives, via a Steglich-type esterification that proceeds in good to excellent yields. Deprotection of the resulting 2-(dimethylphenylsilyl)ethyl acetate was efficiently accomplished using tetrabutylammonium fluoride (TBAF). It is noteworthy, however, that this deprotection led to partial racemization of the amino acid substrates.
Yang et al. (Tue,) studied this question.