A silylation based kinetic resolution of secondary alcohols was reported by the Wiskur group in 2011, employing triphenylsilyl chloride as the silyl source and a chiral isothiourea as the activator.  Recently, mechanistic investigations have been undertaken to elucidate details about the mechanism.  The study presented here employs a linear free energy relationship using different para substituted triphenylsilyl chlorides that vary electronically and sterically.  Selectivity factors and initial rates were determined for reactions run with these new silyl chlorides.  These investigations will be presented along with the trends observed from the data.

Mechanistic analysis of a silylation based kinetic resolution of secondary alcohols

245th National Meeting (2013)

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