Keith Woerpel

Margaret and Herman Sokol Professor of Medicinal Chemistry; Professor of Chemistry
B.S., University of Virginia; A.M., Ph.D., Harvard University; Postdoctoral Fellow, University of California, Berkeley

Phone: 212-998-8772
Office: Silver Center, 100 Washington Square East, Room 825
Lab Homepage

Areas of Research/Interest
Organic chemistry, organic synthesis

Research Description
Our research addresses the development of new methods and reactions for organic synthesis. My laboratory examines transformations with unusual reaction mechanisms that provide insight into fundamental chemical reactivity. As part of this program, we have studied the reactions of strained ring silanes, which led us to develop new reactions of silylenes and to examine the applications of these species in organic synthesis. We have also advanced the understanding of the structures and reactions of oxocarbenium ions, and we have developed stereoelectronic models that explain and predict their reactivity. Our applications of allylic silane chemistry to the synthesis of heterocycles led to the development of several syntheses of natural products, including erythronolide A. We are developing methods for the synthesis of organic peroxides, a family of compounds that includes a large number of biologically active natural products.

Publications"Erosion of Stereochemical Control with Increasing Nucleophilicity: O-Glycosylation at the Diffusion Limit." M. G. Beaver, K. A. Woerpel, J. Org. Chem. 2010, 75, 1107-1118.

"Insertions of Silylenes into Vinyl Epoxides: Diastereoselective Synthesis of Functionalized, Optically Active trans-Dioxasilacyclooctenes." M. Provost, K. A. Woerpel, J. Am. Chem. Soc. 2009, 131, 14182-14183.

"Palladium(II)-Catalyzed Cyclization of Unsaturated Hydroperoxides for the Synthesis of 1,2-Dioxanes." J. R. Harris, S. R. Waetzig, K. A. Woerpel, Org. Lett. 2009, 11, 3290-3293.

"Alkylidenesilacyclopropanes Derived from Allenes: Applications to the Selective Synthesis of Triols and Homoallylic Alcohols." K. M. Buchner, T. B. Clark, J. M. N. Loy, T. X. Nguyen, K. A. Woerpel, Org. Lett. 2009, 11, 2173-2175.

"Formation of Medium-Sized Nitrogen Heterocycles from γ-Silyloxy-γ-Lactams." N. M. Leonard, K. A. Woerpel, J. Org. Chem. 2009, 74, 6915-6923.

"Preparation of Bicyclic 1,2,4-Trioxanes from γ,d-Unsaturated Ketones." A. P. Ramirez, A. M. Thomas, K. A. Woerpel, Org. Lett. 2009, 11, 507-510.

"The Effect of Electrostatic Interactions on Conformational Equilibria of Multiply-Substituted Tetrahydropyran Oxocarbenium Ions." M. T. Yang, K. A. Woerpel, J. Org. Chem. 2009, 72, 545-553.

"C-Glycosylation Reactions of Sulfur-Substituted Glycosyl Donors: Evidence Against the Role of Neighboring-Group Participation." M. G. Beaver, S. B. Billings, K. A. Woerpel, J. Am. Chem. Soc. 2008, 130, 2082-2086.

Outstanding Professor of the School of Physical Sciences, University of California, Irvine (2003 and 2010), Alfred P. Sloan Research Fellowship (2000), AstraZeneca Excellence in Chemistry Award (1999), Camille Dreyfus Teacher-Scholar Award (1998), Cottrell Scholar Award (1997), Glaxo Wellcome Chemistry Scholar Award (1997), Presidential Early Career Award for Scientists and Engineers (1996)

 Update your faculty profile