Department of Chemistry



Ted Cohen

Professor Emeritus


1206 CHVRN

Chevron Science Center 219 Parkman Avenue

Pittsburgh, PA 15260

Research Overview

Development of New Synthetic Methods and Mechanistic Organic Chemistry

Our synthetic mode involves: (1) the design of new chemical reactions often based on our mechanistic studies; (2) sequencing these so as to produce new synthetic methodology; (3) the application of the latter to particularly novel and efficient syntheses of natural products.

The discovery that aromatic radical-anions can reductively cleave C-S bonds has led to some of the most versatile methods known for producing carbanions for synthetic purposes, including the simplest and most general procedures for producing α-lithioethers, α-lithiosilanes, cyclohexenyl- and cycloheptenyllithiums, homoallyllithiums, and allyllithiums.  In the latter case, considerable regiochemical and stereochemical control can be exerted.  One use of these allyllithiums is in the Li-ene cyclization, eventually leading to our study of the analogous Zn-ene cyclization, resulting in perhaps the most efficient synthesis of (-)-kainic acid 1 (see below); an improved procedure that avoids the partial racemization occurring in one of the steps is being developed.

The use of a δ-lithiooxyanion in the most efficient synthesis from commercially available materials of the bee pheromone 2 in its natural pure enantiomeric state is shown.

bee pheromone 2


Ramsay Memorial Fellow (Great Britain), 1955-56

Chancellor's Distinguished Research Award, University of Pittsburgh, 1992

The Pittsburgh Award, Pittsburgh Section, American Chemical Society, 2009.


“Synthesis of (-)-α-Kainic Acid via TMSCl-Promoted Pd-Catalyzed Zinc-ene Cyclization of an Allyl Acetate,” Wei, G.; Chalker, J. M.; Cohen, T., J. Org. Chem., Vol. 76, 2011, Pages 7912-7917
“Readily Prepared 3-Chloro-1-(phenylthio)propene, A Versatile Three-Carbon Annulating Agent,” Liu, T.; Zhao, X.; Lu, L.; Cohen T., Org. Lett., Vol. 11, 2009, Pages 4576-4579
“Enantio- and Diastereoselective Tandem Zn-Promoted Brook Rearrangement/Ene-Allene Carbocyclization Reaction,” Marek, I; Cohen, T.; Chinkov, N.; Stanger, A.; Unger, R.; Weisser, F., Org. Lett., Vol. 11, 2009, Pages 1853-1856
“Enantioselective Ring Expansion of Prolinols. An Efficient and Short Synthesis of 2-Phenylpiperidin-3-ol Derivatives and 3-Hydroxypipecolic Acids,” Cochi, A.; Burger, B.; Navarro, C.; Pardo, D. G.; Cossy, J.; Zhao, Y.; Cohen, T., Synlett, 2009, Pages 2157-2161
“Two Syntheses of (–)‑Kainic Acid via Highly Stereoselective Zinc‑ene Cyclizations,” Chalker, J.; Yang, A.; Deng, K.; Cohen, T., Org. Lett., Vol. 9, 2007, Pages 3825-3828
“Intramolecular Carbozincation of Unactivated Alkenes Occurs Through a Zinc Radical Transfer Mechanism,” Cohen, T.; Gibney, H.; Ivanov, R.; Yeh, E. A.-H.; Marek, I.; Curran, D. P., J. Am. Chem. Soc., Vol. 129, 2007, Pages 15405-15409