INTRODUCTION

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:

Novel 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 rearrangements.

• 1,2-Additions to Activated Imines

• Novel [2,3]-Aza-Wittig Rearrangements

Synthesis of Phosphonamide derivatives of Sildenafil (Viagra™)

Sildenafil (Viagra™) [4], 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.

Novel 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 [5] and Diels-Alder reactions [6]. We are interested in synthesizing related ligands derived from dibenzothiophene. Their reactivity and stereoselectivity would then be investigated in various cornerstone catalytic asymmetric reactions.

[1] S. E. Denmark, R. L. Dorow, J. Org. Chem., 1990, 55, 5926.
[2] K. Afarinkia, A. J. Twist, H. W. Yu, J. Org. Chem., 2004, 69, 6500.
[3] K. Afarinkia, H. Binch, I. Forristal, et al., Phosphorus, Sulfur and Silicon, 2002, 177, 1641.
[4] J. C. Anderson, D. C. Siddons, S. C. Smith, M. E. Swarbrick, J. Org. Chem., 1996, 61, 4820.
[5] K. Nakama, S. Seki, S. Kanemasa, Tetrahedron Letts., 2002, 43, 829.
[6] D. P. Curran, et al., J. Am. Chem. Soc., 1998, 120, 3074.