Asymmetric
Catalysis with "Planar-Chiral Heterocycles":
Nucleophilic Catalysis
November
12, 4:15 pm, 100 Smith
Due
to the "handedness" of
the molecules of life (peptides, DNA, RNA, carbohydrates,
etc.), enantiomeric compounds often display quite different
biological activity. The resulting need to efficiently generate
compounds in enantiopure form (almost all of the Top 10 pharmaceutical
drugs have chiral
active ingredients) has led to burgeoning interest in asymmetric
synthesis, and important progress has been achieved during
the past few decades. Stereoselective reactions that
are based on chiral catalysts, rather than on stoichiometric
chiral reagents or on substrate-bound chiral auxiliaries,
can be advantageous from the standpoints of efficiency and
economy. Three of the most common approaches to accelerating
a chemical
reaction are to employ Brønsted-acid, Brønsted-base,
or Lewis-acid catalysis. A less well-appreciated, but also
common, mode of catalysis is nucleophilic (Lewis-base) catalysis.
We have developed “planar-chiral” derivatives
of 4 (dimethylamino)pyridine (DMAP), a widely
used nucleophilic catalyst, that are effective in a diverse
array of reactions.
|
Announced
Asymmetric Catalysis with "Planar-Chiral Heterocycles":
Transition
Metal-Catalyzed Reactions
November 13, 9:45 am, Smith 331
|
Palladium-
and Nickel-Catalyzed Coupling Reactions
November 15, 9:45 am, Smith
331 |