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Jimmy Wu

 

(Curriculum Vitae)  Professor Wu received his A.B. degree in Chemistry from Princeton University in 1998. He then spent two years as an associate chemist at Merck Process Research where he worked on the development of selective COX-II inhibitors. Afterwards, he moved to Harvard University where he obtained his Ph.D. in organic chemistry from Professor David A. Evans. His doctoral work focused on asymmetric catalysis using lanthanide-pybox complexes. He continued his studies as a postdoctoral fellow with Professor Barry M. Trost at Stanford University where he worked on the synthesis of indoline alkaloid communesin B. He joined the faculty of Dartmouth College in the summer of 2007.

Position: Assistant Professor of Chemistry
E-Mail: jimmy.wu@dartmouth.edu

Phone: 603-646-6481

Address: Department of Chemistry, 6128 Burke Laboratories, Hanover, NH 03755

Newsmakers

Jimmy Wu receives NSF Career Award (CHE 1052824) - "Versatility of Phosphorothioate Esters in the Synthesis of Sulfur-Containing Molecules"

Collaboration with Lorie Loeb (Department of Computer Science) seeks to use animation to teach high school students about organic chemistry

"Better Chemistry Through Cartoons" - Dartmouth NOW (Sept. 21, 2011)

"Wu Animates Study of Science" - The Dartmouth (Oct. 3rd, 2011)

NSF-Sponsored Animations

Screenshots:     

"Adam and Stereochemistry's Big Adventure" can now be viewed on YouTube via this link.

Screenshots:

   

"The Polymer Party" can now be viewed on YouTube via this link.

   

Research Interests

     Although sulfur-containing molecules are prominent in numerous areas of research, comparatively little effort has been devoted to their synthesis. Many well-known bioactive compounds, such as the β-lactam antibiotics (i.e. penicillins, cephalosporins, thienamycin), anti-inflammatory agents (i.e. Vioxx and Celebrex), H2-receptor antagonists (i.e. Tagamet, Zantac, Pepcid), biotin, lipoic acid, and glutathione contain sulfur. In fact, it has been demonstrated in several instances that replacing a carbon or oxygen atom with sulfur greatly enhances the bioactivity of certain compounds with respect to their oxygenated or carbon counterparts. Sulfur-containing compounds also play an important role in organic synthesis as they are useful intermediates in a wide range of diastereoselective and stereospecific transformations. Given the importance of sulfur in chemistry and biology, it is rather surprising that, in comparison to the amount of effort devoted to the discovery of new methods for preparing carbon−carbon, carbon−oxygen, and carbon−nitrogen bonds, considerably fewer resources have been allocated to the development of preparing carbon−sulfur bonds.

     We have developed methods for constructing carbon-sulfur bonds by direct displacement of the corresponding alcohol and/or other oxygen-based leaving groups using catalytic Ga(OTf)₃ or UV light.  In particular, our laboratory has demonstrated that phosphorothioate esters are versatile functional groups that can be transformed into thiols, thioethers, and enantioenriched tetrahydrothiophenes.  We have also shown that allylic phosphorothioate esters readily participate in transition metal-catalyzed cross-coupling reactions with a diverse range of Grignard reagents to furnish carbon-carbon bonds.

Selected Publications

Publications While at Dartmouth

"Phosphorothioic Acids as Surrogates for H₂S - Synthesis of Chiral Tetrahydrothiophenes" Robertson, F. J.; Wu, J. J. Am. Chem. Soc. 2012, 134, 2775-2780.

“Cu(I)-Catalyzed, alpha-Selective, Allylic Alkylation Reactions between Phosphorothioate Esters and Organomagnesium Reagents” Lauer, A. M.; Mahmud, F.; Wu, J. J. Am. Chem. Soc. 2011, 133, 9119−9112. (This report was highlighted in Synfacts 2011, 9, 1009.)

“Direct Annulation and Alkylation of Indoles with 2-Aminobenzyl Alcohols Catalyzed by TFA” Robertson, F. J.; Kenimer, B. D.; Wu, J. Tetrahedron 2011, 67, 4327-4332. (Invited Contribution - Symposium in Print: Tetrahedron Young Investigators Award for Prof. Dean Toste)

“Ga(OTf)₃-Catalyzed Direct Substitution of Alcohols with Sulfur Nucleophiles” Han, X.; Wu, J. Org. Lett. 2010, 12, 5780−5782.

“Convenient Synthesis of Allylic Thioethers from Phosphorothioate Esters and Alcohols” Robertson, F. J.; Wu, J. Org. Lett. 2010, 12, 2668−2671.

“Mild Two-Step Process for the Transition-Metal-Free Synthesis of Carbon−Carbon Bonds from Allylic Alcohols/Ethers and Grignard Reagents” Han, X.; Zhang, Y.; Wu, J. J. Am. Chem. Soc. 2010, 132, 4104−4106. (This report was highlighted in Synfacts 2010, 6, 700.)

Other Publications

• “Stereoselective Preparation of a Cyclopentane-Based NK1 Receptor Antagonist Bearing an Unsymmetrically Substituted Sec-Sec Ether” Kuethe, J. T.; Marcoux, J. -F.; Wong, A.; Wu, J.; Hillier, M. C.; Dormer, P. G.; Davies, I. W.; Hughes, D. L. J. Org. Chem. 2006, 71, 7378−7390.
• “Asymmetric, anti-Selective Scandium-Catalyzed Sakurai Additions to Glyoxamide. Applications to the Syntheses of N-Boc d-Alloisoleucine and d-Isoleucine” Evans, D. A.; Aye, Y.; Wu, J. Org. Lett. 2006, 8, 2071−2073.
• “Enantioselective Syn-Selective Scandium-Catalyzed Ene Reactions” Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2005, 127, 8006−8007.
• “Enantioselective Rare-Earth Catalyzed Quinone Diels-Alder Reactions” Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162−10163.
• “A General Method for the Enantioselective Synthesis of Pantolactone Derivatives” Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379−3382.
• “C2-Symmetric Sc(III)–Complexes as Chiral Lewis Acids. Catalytic Enantioselective Aldol Additions to Glyoxylate Esters” Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375−3378.
• “Asymmetric Synthesis of 1,2,3-Trisubstituted Cyclopentanes and Cyclohexanes as Key Components of Substance P Antagonists” Kuethe, J. T.; Wong, A.; Wu, J.; Davies, I. W.; Dormer, P. G.; Welch, C. J.; Hillier, M. C.; Hughes, D. L.; Reider, P. J. J. Org. Chem. 2002, 67, 5993−6000.
• “Experimental and Theoretical Studies on the Oxidative Addition of Palladium (0) to Salts” Davies, I. W.; Wu, J.; Marcoux, J.-F.; Taylor, M.; Hughes, D.; Reider, P. J.; Deeth, R. J. Tetrahedron 2001, 57, 5061−5066.
• “β-Regioselective Intermolecular Heck Arylation of N,N-Disubstituted Allylamines” Wu, J.; Marcoux, J.-F.; Davies, I. W.; Reider, P. J. Tetrahedron Lett. 2001, 42, 159−162.
• “A General Preparation of Pyridines and Pyridones Via the Annulation of Ketones and Esters” Marcoux, J.-F.; Marcotte, F.-A.; Wu, J.; Dormer, P. G.; Davies, I. W.; Hughes, I. W.; Reider, P. J. J. Org. Chem. 2001, 66, 4194−4199.
• “Preparation and Novel Reduction Reactions of Vinamidinium Salts” Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251−255.
• “Stereoselective Hydrogen Bromide-Promoted Hydrogenation of an α-Hydroxy Oxime” Davies, I.W.; Taylor, M.; Marcoux, J.-F.; Matty, L.; Wu, J.; Hughes, D.; Reider, P. J. Tetrahedron Lett. 2000, 41, 8021−8025.