Professor (b. 1949). B.S., 1971, University of Wisconsin-Eau Claire; Ph.D., 1979, Iowa State University; NIH Postdoctoral Fellow, 1979-80, Princeton University.
517-355-9715, Ext. 373
SYNTHETIC ORGANIC CHEMISTRY
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William
D. Wulff
Professor (b. 1949). B.S., 1971, University of Wisconsin-Eau Claire; Ph.D., 1979, Iowa State University; NIH Postdoctoral Fellow, 1979-80, Princeton University. 517-355-9715, Ext. 373 |
Our research areas of interest include methodology development, macrocyclic chemistry, organometallic chemistry, the total synthesis of natural products, supramolecular chemistry, and the design and development of new asymmetric catalysts. Several new reactions of transition metal carbene complexes complexes with potential applications in synthetic organic chemistry are being investigated. These include the benzannulation reaction with acetylenes, Diels-Alder reactions, Michael additions, Aldol reactions, C-H insertions, cyclopropanations, [3 + 2] cycloadditions and [2 + 2] cycloadditions. Synthetic targets for which these reactions are being evaluated include indole alkaloids, steroids, taxol, fostriecin, aureolic acids, phomactin D and longithorone A. Another area of interest involves the development of new chiral ligands for catalysts in asymmetric synthesis. A new family of chiral biaryls has been developed which can be used as chiral ligands for various metal based Lewis acids that provide chiral catalysts that give asymmetric induction and turnover numbers that are superior to existing catalysts. The evaluation of these ligands in Diels-Alder, allylation, Michael additions, reductive amination and aziridination reactions are currently being investigated. We have recent developed the first generally useful catalytic asymmetric aziridination reaction with a catalyst that was prepared from the VAPOL ligand. A new program involves the design of chiral macrocycles as catalysts in asymmetric synthesis.
Calixalyst for the
asymmetric
Fostriecin
cyclopropanation of alkenes
VAPOL
Taxol
Representative Publications
A Novel Strategy for the Synthesis of Taxol: The Use of Fischer Carbene Complexes in the Preparation of Bicyclo[3.1.1]heptanones as Taxane A-ring Synthons, W. Jiang, M. J. Fueretes, and W. D. Wulff, Tetrahedron, 56, 2183 (2000).
Mechanistic Studies on the Reaction of Fischer Carbene Complexes with Alkynes. Does the Alkyne Insertion Intermediate form Irreversibly? M. L. Waters, M. E. Bos, and W. D. Wulff, J. Am. Chem. Soc., 121, 6403 (1999).
Catalytic Asymmetric Aziridination with a Chiral VAPOL-Boron Lewis Acid, J. C. Antilla and W. D. Wulff, J. Am. Chem. Soc., 121, 5099 (1999).
Novel [1,5] Sigmatropic Rearrangements of Cyclohexadienones Generated from Fischer Carbene Complexes. A New Strategy for Installing the C-20 Angular Ethyl Group in Aspidospermidine Alkaloids, J. F. Quinn, M. E. Bos, and W. D. Wulff, Organic Letters, 1, 161 (1999).
Macrocyclization of Fischer Carbene Complexes as an Approach to Cyclophanes, H. Wang and W. D. Wulff, J. Am. Chem. Soc., 120, 10573 (1998).