Asymmetric Silylation of Secondary Alcohols

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Presentation transcript:

Asymmetric Silylation of Secondary Alcohols Sheryl L. Wiskur University of South Carolina Department of Chemistry & Biochemistry The kinetic resolution of secondary alcohols is an important transformation for the preparation of chiral building blocks. While there are a number of ways to selectively derivatize one enantiomer over another, the use of a silyl group has been virtually ignored. The two different approaches we are investigating rely on (1) the resolution of diastereomeric salts from a Mukaiyama reaction and (2) chiral nucleophilic activation of silyl protecting groups where the catalysts are derived from cinchona alkaloids. Both approaches offer the ability to asymmetrically purify racemic substrates in order to obtain enantiomerically pure compounds. This research has explored the fundamentals of these reactions, looking at the mechanisms and the effects of sterics and electronics. The broader impacts of this research include providing a much needed synthetic tool to the organic community as well as training students in a variety of different techniques and paradigms as they become successful chemists .