Professor Amir Hoveyda
Boston College
Harnessing Fluorine-‐Induced Ion–
Dipole Attractive Forces in
Enantioselective Catalysis
Tuesday
May 26th, 2015
3:30 pm
Room 1315
Chemistry
The impact of organofluorine compounds in human
medicine, agrochemicals and materials research has
been prominent. Better understanding of the influence
of fluorine atoms on physical characteristics and ability
of their host molecules to interact with other entities,
particularly in the liquid phase (vs. X-‐ray
crystallography), is therefore crucial. What’s more,
because identification of desirable organofluorine
compounds is almost exclusively the purview of
laboratory synthesis and screening protocols (vs.
natural products), development of efficient and
broadly applicable catalytic transformations that
furnish such molecules in high enantiomeric purity
constitutes a compelling objective. In this Lecture, we
will see how ammonium/F–C electrostatic (ion–dipole)
attractions might play a critical role in controlling the
enantioselectivity of additions of organoboron reagents
to fluoro-‐substituted ketones. The electrostatic
influence of different types of fluoro-‐organic moieties
on enantioselectivity and their interplay with other
more familiar dipolar and/or steric forces will be a
topic of discussion as well.