Dept. of Chemistry

Daniel C. Whitehead

Photo of Dan WhiteheadAssistant Professor
Organic Chemistry

Phone: (864) 656-5765
Office: 467 Hunter
E-mail: dwhiteh@clemson.edu

Research Interests | Publications

Dr. Whitehead received his B.S. (2002) and M.S. (2003) degrees in chemistry from Furman University, working in the labs of Professor Larry Trzupek.   He earned his Ph. D. (2009) from Michigan State University under the mentorship of Professor Babak Borhan.  His doctoral research focused on the development of novel asymmetric olefin halogenation reactions culminating in the development of an asymmetric chlorolactonization protocol.  He was a postdoctoral fellow (2009-2011) at North Carolina State University in the labs of Professor Christian Melander.  His postdoctoral studies focused on the development of novel therapeutics including anti-biofilm agents, osteoclastogenesis inhibitors, and nanoparticle-drug conjugates for the treatment of HIV infections.  Dr. Whitehead joined the Clemson University Chemistry Department in 2011.

Research Interests

In general terms, research in Dr. Whitehead’s labs focuses on the development of new organic methodology.  We are interested in developing new approaches for the efficient transformation of readily available feed-stock chemicals to generate richly functionalized, high value small molecules for a variety of applications.  Particular emphasis is placed on rendering such transformations asymmetric.  Specifically our efforts are divided into three sub-aims.

1. The development of an organocatalytic vicinal diamination of olefins.  We aim to exploit azodicarboxylate/phosphine betaines as novel reagents for reaction with alkenes to generate diazetidine products, thus effecting a formal vicinal diamination.  Subsequent efforts will focus on rendering the overall process catalytic and asymmetric.  We will also investigate novel transformations of the diazetidine products to generate other interesting scaffolds.

2. The use of boronate esters as chiral control elements in the Diels-Alder cycloaddition.  We are interested in developing appropriate chiral boronate esters containing diene or dienophile components and employing them as chiral control elements in the Diels-Alder cycloaddition.   We will then employ the unique functionality embedded within the cyclic boronate ester products to explore further transformations.

3. The development of modified peptides for use as asymmetric catalysts and ligands.  We will design and synthesize small peptide conjugates equipped with appropriate active site scaffolds for use as chiral catalysts and ligands.  We will investigate the incorporation of aryl-iodo active sites into a peptide framework for use as asymmetric catalysts for hypervalent iodine mediated transformations.  Additionally, we will design and synthesize novel olefin containing amino acids to generate novel olefin ligands for rhodium and osmium based transformations.

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Publications

9. Whitehead, D. C.; Fhaner, M.; Borhan, B. “A Peptide Bromoiodinane Approach Toward Asymmetric Bromolactonization” Tetrahedron Lett. 2011, 52, 2288.

8. Jaganathan, A.; Garzan, A.; Whitehead, D. C.; Staples, R. J.; Borhan, B. “A Catalytic Asymmetric Chlorocyclization of Unsaturated Amides” Angew. Chem. Int. Ed. 2011, 50, 2593.

7. Yousefi, R.; Whitehead, D. C.; Mueller, J. M.; Staples, R. J.; Borhan, B. “On the Terminal Chlorenium Source in the Asymmetric Chlorolactonization Reaction” Org. Lett. 2011, 13, 608.

6. Rogers, S. A.; Lindsey, E. L.; Whitehead, D. C.; Mullikin T.; Melander, C. “Synthesis and Biological Evaluation of 2-Aminoimidazole/Cabamate Hybrid Anti-Biofilm and Anti-Microbial Agents” Biorg. Med. Chem. Lett. 2011, 21, 1257.

5. Rogers, S. A.; Whitehead, D. C.; Mullikin, T.; Melander, C. “Synthesis and Bacterial Biofilm Inhibition Studies of Ethyl N-(2-phenethyl) carbamate derivatives” Org. Biomol. Chem. 2010, 8, 3857.

4. Whitehead, D. C., Yousefi, R., Jaganathan, A.; Borhan, B. “An Enantioselective Organocatalytic Chlorolactonization” J. Am. Chem. Soc.  2010, 132, 3298.

3. Whitehead, D. C.; Staples, R. J.;  Borhan, B. “A Simple and Expedient Method for the Preparation of N-Chlorohydantoins” Tetrahedron Lett. 2009, 50, 656.

2. Whitehead, D. C.; Travis, B. R.; Borhan, B. “The OsO4-mediated Oxidative Cleavage of Olefins Catalyzed by Alternative Osmium Sources” Tetrahedron Lett. 2006, 47, 3797

1. Choi, D.-S.; Chong, Y.S.; Whitehead, D.; Shimizu, K.D. “Molecules with Shape Memory Based on Restricted Rotation” Org. Lett. 2001, 3, 3757

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