Office: 564 Science and Technology Building
Telephone: (252) 328-9798
Fax: (252) 328-6210
Department of Chemistry
|Organometallic chemistry bridges
the gap between organic and inorganic chemistry, with applications ranging
from material science to organic synthesis. My research interests
focus on the catalytic applications of transition metal complexes with synthetic
organic applications. Summarized below is the current research ongoing in
my group, including future plans. Mechanistic and structural studies are
necessary parts of this program, and ab initio calculations will be applied
when appropriate. One of the points that will be emphasized in my
research group will be the development of catalyst systems that are useful
at practical temperatures and pressures, and possibly under less than anaerobic
or moisture free conditions.
The primary project ongoing in the Morehead Group is the synthesis of chiral indanones via intramolecular hydroacylation. As illustrated in Equation 1, we have discovered that the rhodium-catalyzed ring closure of vinylbenzaldehydes proceeds in very high yields and with ee’s as high as 99.4% using BINAP as the chiral ligand.
|During the exploratory work with
the above system, we discovered an interesting dimerization (Equation 2).
Curiously, addition of an excess of styrene does not result in incorporation
of styrene into the tetrahydronaphthalene. Preliminary experiments
to elucidate the mechanism have led us to believe that interaction between
the pi system of the aromatic ring and the metal may be crucial to this
novel form of reactivity.
Further exploration of the limits of the chiral hydroacylation reaction is planned, as well as mechanistic work designed to elucidate the mechanism of the unusual dimerization we observed.
As mentioned above, we have evidence that there may be an interaction between the pi system of the arene and the metal. We plan to investigate the cyclization of substrates such as that shown in Equation 3, which we should be able to force to either the cycloadduct or the indanone by choice of reaction conditions. Either product is useful in the synthesis of natural products or pharmaceuticals, particularly in a chiral form.
East Carolina University
Greenville, NC 27858