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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 .