The kinetic resolution of secondary alcohols is an important transformation in asymmetric chemistry.  While there are a number of great methods available, a majority of the work has focused on selective acylation with silylation-based kinetic resolutions only recently gaining interest.  We are focused on promoting enantioselective silylation of racemic alcohols by employing chiral isothiourea catalysts and triphenylsilyl chlorides.  The resolution of different alcohol classes has been possible, including secondary cyclic alcohols, a-hydroxy carbonyl compounds, and 2-aryl cyclic alcohols.  We are also exploring the mechanism through linear free energy relationships, kinetics, and NMR experiments.  The substrate scope and mechanistic investigations will be presented.

Kinetic resolutions by silylation: Substrate scope and mechanistic investigations

248th National Meeting (2014)

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