A silylation based kinetic resolution of monofunctional secondary alcohols has been developed by the Wiskur group. This methodology has achieved a high level of selectivity using triphenylsilyl chloride as the silicon source. For further expansion, a deeper understanding of the mechanism will provide detailed insight into our methodology. We will discuss our efforts towards this through the use of linear free energy relationships revolving around the silicon protecting group. The effects of electronics and sterics at silicon will be elucidated.

Mechanistic investigations of a silylation based kinetic resolution of secondary alcohols

243rd National Meeting (2012)

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