My research interests lie in the
fields of synthetic organic chemistry, asymmetric synthesis
and medicinal chemistry. We are particularly interested in utilizing
oragnophosphorus and organosulfur compounds as “chiral
auxiliaries” and “chiral catalysts” for the
development of novel asymmetric methodology. Our objective is
the stereoselective synthesis of important chiral building blocks
and their application in the synthesis of biologically active
compounds. Click on the links below for a brief outline of my
current and future research projects for both senior undergraduate
and graduate students:
Applications of Chiral Phosphorus Auxiliaries
Recently, several research groups
have demonstrated that 2-oxo-1,3,2-oxazaphosphorinanes are a
powerful class of chiral auxiliary [1-3]. Two of our current
research programs employ this class of chiral phosphorus auxiliary
in order to control the stereoselectivity of several cornerstone
asymmetric processes such as additions to imines and sigmatropic
1,2-Additions to Activated Imines
Novel [2,3]-Aza-Wittig Rearrangements
of Phosphonamide derivatives of Sildenafil (Viagra™)
Sildenafil (Viagra™) , Pfizer's
world renowned treatment for male erectile dysfunction has rapidly
become one of the largest selling globally marketed prescription
drugs. We are interested in synthesizing various phosphonamide
analogues in order to yield novel Sildenafil derivatives.
Chiral Lewis Acid Catalysts derived from Dibenzothiophene
Chiral Lewis acid catalysts incorporating
the DBFOX ligand have been used with some success in asymmetric
conjugate additions  and Diels-Alder reactions . We are
interested in synthesizing related ligands derived from dibenzothiophene.
Their reactivity and stereoselectivity would then be
investigated in various cornerstone catalytic asymmetric reactions.
 S. E. Denmark, R. L. Dorow,
J. Org. Chem., 1990, 55, 5926.
 K. Afarinkia, A. J. Twist, H. W. Yu, J. Org. Chem., 2004,
 K. Afarinkia, H. Binch, I. Forristal, et al., Phosphorus,
Sulfur and Silicon, 2002, 177, 1641.
 J. C. Anderson, D. C. Siddons, S. C. Smith, M. E. Swarbrick,
J. Org. Chem., 1996, 61, 4820.
 K. Nakama, S. Seki, S. Kanemasa,
Tetrahedron Letts., 2002, 43, 829.
 D. P. Curran, et al., J. Am. Chem. Soc., 1998,