Chemistry at Illinois University of Illinois at Urbana-Champaign

Scott E. Denmark

Reynold C. Fuson Professor of Chemistry

Professor Scott E. Denmark received his undergraduate degree from the Massachusetts Institute of Technology in 1975 and his graduate degree (D.Sc. Tech.) from the ETH-Zürich in 1980. He joined the faculty at Illinois in the same year. His research interests are in structural, synthetic and mechanistic organic chemistry.

Research

The research in my group is primarily involved with the invention of new synthetic reactions, on the origin of stereocontrol in fundamental carbon-carbon and carbon-heteroatom bond forming reactions, in the application of these developments to the synthesis of complex molecular structures and in catalysis. A continuing theme of the work in these laboratories is the relationship between structure, reactivity and stereoselectivity in a variety of organo-element systems, particularly, silicon, phosphorus, tin, sulfur and lithium-containing compounds. We have pioneered the concept of chiral Lewis base activation of Lewis acids for catalysis in main group synthetic organic chemistry and have successfully applied this concept to myriad enantioselective carbonyl addition reactions (with silicon) and olefin functionalization reactions (with halogens and chalcogens). In recent years our interest has also focused on palladium catalyzed cross-coupling reactions with organofunctional silicon compounds. We have maintained a long-standing interest in the development and application of tandem heterodiene cycloadditions for the synthesis of complex natural (alkaloids) and unnatural (fenestranes) nitrogen containing compounds. Our interest in catalysis is currently leading us to investigate the structure-activity-selectivity principles in phase transfer catalysis.

Publications

Total Synthesis of Isodomoic Acids G and H (with J.H.-C. Liu and J.M. Muhuhi) J. Am. Chem. Soc. 2009, 131, 14188-14189.

On the Mechanism of Lewis Base Catalyzed Aldol Addition Reactions: Kinetic and Spectroscopic Investigations Using Rapid-Injection NMR (with B.M. Eklov, P.J. Yao, and M.D. Eastgate) J. Am. Chem. Soc. 2009, 131, 11770-11787.

Observation of Direct Sulfenium and Selenium Group Transfer from Thiiranium and Seleniranium Ions to Alkenes (with W.R. Collins and M.D. Cullen) J. Am. Chem. Soc. 2009, 131, 3490-3492.

Palladium- (and nickel-) catalyzed vinylation of aryl halides (with C. R. Butler) Chem. Commun. 2009, 20-33

Cross-Coupling of Aromatic Bromides with Allylic Silanolate Salts (with N. S Werner) J. Am. Chem. Soc. 2008, 130, 16382-16393.

Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and their Salts: A Practical Alternative to Boron- and Tin-based Methods (with C. S. Regens) Acc. Chem. Res. 2008, 41, 1486-1499.

Asymmetric Synthesis of the ABCD Ring System of Daphnilactone B via a Tandem, Double Intramolecular [4+2]/[3+2] Cycloaddition Strategy (with R. Y. Baiazitov and S. Nguyen) Heterocycles (Dedicated Issue to Ryoji Noyori) 2008, 76, 143-154.

Vinylation of Aromatic Halides Using Inexpensive Organosilicon Reagents Illustration of Design of Experiment Protocols (with Christopher R. Butler) J. Am. Chem. Soc. 2008, 130, 3690-3704.

Lewis Base Catalysis in Organic Synthesis (with G. L. Beutner) Angew. Chem. Int. Ed. 2008, 47, 1560-1638.

"Total Synthesis of Papulacandin D" (with C. R. Regens and T. Kobayashi) J. Am. Chem. Soc. 2007, 129, 2774-2776.

"Lewis Base Activation of Lewis Acids: Catalytic, Enantioselective Vinylogous Aldol Addition Reactions" (with J. R. Heemstra) J. Org. Chem. 2007, 72, 5668-5688.

Awards

  • Fellow, American Chemical Society
  • Herbert C. Brown Award for Creative Research in Synthetic Methods (American Chemical Society)
  • Recipient, Robert Robinson Lectureship (Royal Society of Chemistry, England)
  • Prelog Medal
  • Fellow, Royal Society of Chemistry
  • Yamada-Koga Prize (Japan Research Foundation for Optically Active Compounds)
  • ACS Award for Creative Work in Synthetic Organic Chemistry
  • Pedler Medal (Royal Society of Chemistry)
  • Fellow, AAAS
  • Alexander Von Humboldt Senior Scientist Award
  • A.C. Cope Scholar Award, American Chemical Society
  • Stuart Pharmaceuticals Award in Chemistry, ICI Americas
  • University Scholar, University of Illinois
  • Procter and Gamble University Exploratory Research Program Award
  • NSF Presidential Young Investigator Award
  • A.P. Sloan Foundation Fellow
  • Eli Lilly Research Award

Highlights

Patents

Photo of Scott E. Denmark