Professor, Organic Chemistry
(414) 288-7374
E-mail: william.donaldson@mu.edu
Biography
Professor Donaldson received his B.A. in 1977 from Wesleyan University and his Ph.D. degree in organometallic chemistry from Dartmouth College in 1981. He was a Postdoctoral Research Associate at Brandeis University (1981-82) and a Visiting Assistant Professor at Wesleyan (1982-83) before joining the faculty at Marquette University in August 1983. Professor Donaldson was awarded the Edward D. Simmons Award for Junior Faculty Excellence (1988), the Rev. John R. Raynor Faculty Award for Teaching Excellence (1995), and a Alexander von Humboldt Research Fellow at Philipps- Universitaet Marburg, Germany (1990-91).
Research Fields
For a number of years, we have examined the reactivity of open pentadienyl iron cations (1) with nucleophiles. Through these studies we have observed nucleophilic attack at both the terminal carbon atoms (path a) and at internal positions (path b). The regioselectivity of these reactions depend on the substitutents present on the pentadienyl ligand, the "spectator" ligands attached to iron, and the nature of the nucleophile (ie. heteroatom nucleophiles, or organolithiums, or stabilized carbon nucleophiles). Where these reactions proceed with high regioselectivity, they can be utilized for the formation of carbon- nucleophile bonds in the synthesis of compounds of biological interest (eg. terpenes, pheromones, oxygenated metabolites).
Targets molecules of interest are macrolactin A (2), protomycinolide IV (3), streptenol D (4) and ambruticin (5).
Selected Publications
- Y. K. Yun, K. Godula, Y. Cao, and W. A. Donaldson, "Iron Mediated Preparation of Vinylcyclopropanes. Scope, Mechanism, and Applications", J. Org. Chem. 2003, 68, 901-910.
- J. M. Lukesh and W. A. Donaldson, "Synthesis of (+)-Decarestrictine L", Tertrahedron: Asymmety 2003, 14, 757-762.
- Z. He, C. S. Yi, and W. A. Donaldson, "Regio- and Stereoselective Ruthenium Catalyzed Hydrovinylation of 1,3-Dienes: Application to the Generation of a 20S-Steroidal Sidechain", Org. Lett. 2003, 5, 1567-1569.
- S. Li and W. A. Donaldson, "Enantioselective Synthesis of the C7-C24 Segment of Macrolactin A", Synthesis, 2003, 2064-2068.
- N. Wallock and W. A. Donaldson, "Reactivity of (Bicyclo[5.1.0]octadienyl)iron(1+) Cations: Application to the Synthesis of cis-2-(2’-carboxycyclopropyl)glycines", J. Org. Chem. 2004, 69, 2997-3007.
- J. M. Lukesh and W. A. Donaldson, "Synthesis of Cyclopropanes via Organoiron Methodology: Preparation of the C9-C16 Alkenylcyclopropane Segment of Ambruticin", Chem. Comm. 2005, 110-112.
- N. J. Wallock and W. A. Donaldson, "Synthesis of Cyclopropanes via Organoiron Methodology: Preparation and Rearrangement of Divinylcyclopropanes", Org. Lett. 2005, 7, 2047-2049.
- S. Chaudhury and W. A. Donaldson, “Nucleophilic Addition to (3-Methylpentadienyl)iron(1+) Cations: Counterion Control of Regioselectivity; Application to the Enantioselective Synthesis of 4,5-Disubstituted Cyclohexenones”, J. Am. Chem. Soc. 2006, 128, 5984-5985.
- S. Chaudhury, S. Li and W. A. Donaldson, “Synthetic studies directed toward the proposed structure for heteroscyphic acid A”, Chem. Comm. 2006, 2069-2070.
Klingler College of Arts & Sciences
