Dr. Wade Downey
Assistant Professor of Chemistry
C-311 Gottwald Center for the Sciences
Office: (804) 484-1557
Fax: (804) 287-1897
Speciality:
Organic Chemistry
Teaching:
Organic Chemistry I and II
Research:
We are interested in the development of one-pot and tandem reactions that reduce the need for expensive and time-consuming purification processes. We approach this goal through two fronts: 1) Our silylation-driven chemistry employs TMSOTf as both a silylating agent and a Lewis acid, allowing rapid access to Mukaiyama aldol products directly from unactivated ketones, esters, thioesters, and amides. Similarly, we are studying the addition of unactivated terminal acetylenes to various electrophiles in the presence of TMSOTf and catalytic zinc salts. 2) We are developing one-pot conjugate addition-oxidation-Diels¿Alder reactions of ynoates, in which three separate reactions are controlled to provide a stereochemically enriched product. All of our new reactions should prove beneficial to a pharmaceutical industry constantly seeking new methods to make new drug targets and known drugs more efficiently.
Education:
Ph.D., Harvard University
Selected Publications:
C. Wade Downey, Brian D. Mahoney, Vincent R. Lipari “Trimethylsilyl Trifluoromethanesulfonate-Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes” Journal of Organic Chemistry 2009, 74, 2904-2906.
C. Wade Downey, Miles W. Johnson, Kathryn J. Tracy “One-Pot Enol Silane Formation-Mukaiyama Aldol-Type Addition to Dimethyl Acetals Mediated by TMSOTf” Journal of Organic Chemistry 2008, 73, 3299-3302.
C. Wade Downey, Miles W. Johnson "A Tandem Enol Silane Formation-Mukaiyama Aldol Reaction Mediated by TMSOTf" Tetrahedron Letters 2007, 48, 3559-3562.
A. Suarez, C.W. Downey, G.C. Fu "Resolutions of Azomethine Imines via Cu-Catalyzed [3+2] Cycloadditions" Journal of the American Chemical Society 2005, 127, 11244-11245.T.E. Smith, M. Djang, A.J. Velander, C.W. Downey, K.A. Carroll, S. van Alphen "Versatile Asymmetric Synthesis of Kavalactones: First Synthesis of (+)-Kavain" Organic Letters 2004, 6, 2317-2320.
D.A. Evans, C.W. Downey, J.L. Hubbs "Ni(II) Bis(oxazoline)-Catalyzed Enantioselective Syn Aldol Reactions of N-Propionylthiazolidinethiones in the Presence of Silyl Triflates" Journal of the American Chemical Society 2003, 125, 8706-8707.
D.A. Evans, C.W. Downey, J.T. Shaw, J.S. Tedrow "Magnesium Halide-Catalyzed Diastereoselective anti-Aldol Reactions of Chiral N-Acylthiazolidinethiones" Organic Letters 2002, 4, 1127-1130.
D.A. Evans, J.S. Tedrow, J.T. Shaw, C.W. Downey "Diastereoselective Magnesium Halide-Catalyzed anti-Aldol Reactions of Chiral N-Acyloxazolidinones" Journal of the American Chemical Society 2002, 124, 392-393.
