Jeffrey Bode

Associate Professor of Chemistry
Organic Chemistry

Office: IAST 2002
Phone: 215 573 1953
Email: bodesasupennedu
Research Group Website: http://www.bodegroup.org

Jump to: Research Statement | Education and Academic History | Selected Publications

Research Statement
Overview: Research in our group seeks to bring the experience and tactics of natural product total synthesis and the strategies of organic methodology development to bear on contemporary problems in reaction discovery, molecular biology, and materials science. Although the synthesis of organic molecules remains the cornerstone of our approach, we believe the molecules and methods developed in our laboratory will have wide ranging applications in emerging areas.

Chemoselective Ligation Reactions: Chemical ligation reactions allow for the assembly of two fragments regardless of the structure and functionality in the vicinity of the coupling site. To achieve this, we are devising new chemical reactions, which allow unprotected molecules to be chemoselectively coupled together by a highly specific reaction whose success depends only on the presence of the appropriate functionality in the ligation substrates.
We have succeeded in developing the first general method for amide-forming chemical ligation under aqueous conditions without the use of reagents or the production of byproducts (Bode et al., Angew. Chem. Int. Ed. 2006, 1248–1252). Our preliminary results demonstrate the potential of this process to significantly impact the preparation of proteins, glycopeptides, and related structures by the highly selective coupling of unprotected fragments. This chemistry is being applied to the synthesis of peptide and protein-based structures, especially highly modified molecules containing unnatural appendages. Further applications of this remarkable process include new directions in the synthesis and functionalization of biocompatible materials.
While chemoselective approaches to amides remains a primary focus, we are also developing new chemoselective reactions for accessing key chemical linkages present in biological molecules including esters, amines, phosphodiesters, and glycosyl bonds.

New Reactions Catalyzed by N-Heterocyclic Carbenes: We have recently pioneered the catalytic generation of reactive intermediates by N-heterocyclic carbene (NHC) catalyzed internal redox reactions of functionalized aldehydes. These organocatalytic reactions allow the transient formation of activated carboxylates, homoenolates, and enolates under exceptionally mild, simple reaction conditions and additional reagents or by-products. We have utilized these novel processes for the synthesis of chiral, enantiomerically enriched esters, amides, lactones, lactams, and carbocyclic structures. Ongoing mechanistic investigations and applications of these catalytic reactions to the synthesis of biologically active molecules continue to lead to new discoveries and powerful reaction manifolds.

Adaptive Organic Molecules: We are exploiting unique organic reactions to develop small organic molecules (mw 200 - 1500) with the ability to rapidly change their chemical and physical properties without chemical reagents. Using synthetic organic chemistry and reaction development, along with inspiration from natural products and physical organic chemistry, we are synthesizing molecular entities that can morph themselves into thousands of different constitutional isomers, thus modulating their chemical and physical properties.

Education and Academic History

Selected Publications
Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. "Enantioselective, Cyclopentene-Forming Annulations via NHC-Catalyzed Benzoin–Oxy-Cope Reactions", J. Am. Chem. Soc. 2007, 129, 3520–3521.

He, M.; Uc, G. J.; Bode, J. W. “Chiral N-Heterocyclic Carbene Catalyzed Oxodiene Diels-Alder Reactions with Low Catalyst Loadings”, J. Am. Chem. Soc. 2006, 128, 15088–15089.

Lippert, A. R.; Kaeobamrung, J.; Bode, J. W. “Synthesis of Oligosubstituted Bullvalones: Shapeshifting Molecules Under Basic Conditions”, J. Am. Chem. Soc. 2006, 128, 14738–14739.

Carrillo, N.; Davalos, E. A.; Russak, J. A.; Bode, J. W. “Iterative, Aqueous Synthesis of beta(3)-Oligopeptides without Coupling Reagents”, J. Am. Chem. Soc. 2006, 128, 1452–1453.

Bode, J. W.; Fox, R. M.; Baucom, K. D. “Decarboxylative Condensations of alpha-Ketoacids and N-Alkylhydroxylamines: A New Amide Ligation Reaction”, Angew. Chem. Int. Ed. 2006, 45, 1248–1252.

Sohn, S. S.; Rosen, E. L.; Bode, J. W. “N-Heterocyclic Carbene Catalyzed Generation of Homoenolates: Butyrolactones by Direct Annulations of Enals and Aldehydes”, J. Am. Chem. Soc. 2004, 126, 14370–14371.

Chow, K. Y.-K.; Bode, J. W. “Catalytic Generation of Activated Carboxylates: Direct, Stereoselective Synthesis of beta-Hydroxyesters from Epoxyaldehydes” J. Am. Chem. Soc. 2004, 126, 8126–8127.