CHEM 634 Presentation Assignment Goal To understand a recent methodology and/or synthesis paper and be able to explain it to others, including a critical explanation of prior art in the field, why this paper represents a significant advance, and the related work that emerged after this paper Deadlines Thurs, Oct 16, 2pm Choose your paper. You must note your choice on the sign-up Google doc. Link to the Google doc: https://docs.google.com/a/udel.edu/spreadsheets/d/1_Z5Nt15FuHOPggdpnaQFQJ KFWTKT43qU8F0xMlif9K8/edit?usp=sharing Thurs, Nov 20, 5pm Presentations emailed to Mary. Mary will compile the presentations and email all of them to the class by Fri, 11/21, 5pm. Sat, Nov 21, 9am–12noon Special Saturday Presentations, room TBA Bagels will be provided. Guidelines The grade you earn on your presentation represents 15% of your overall grade. I will set the order of presentations on Sat, Nov 21. Presentations should be professional in appearance and content. Use ChemDraw (or an analogous program) for schemes (DO NOT JUST COPY AND PASTE SCHEMES FROM THE PAPER!!!). You should use PowerPoint (or an analogous program) for the presentation. Your slides should look nice and clearly convey your message!!! Presentations should be 10 min long. We will take about 5 min for questions and discussion for each presentation. Your presentation should explain why the paper is important, including a review of prior and later literature. You should be prepared to intelligently answer questions about all aspects of the paper and their methods. Grading for the presentation will include content and coverage of the topic, as well as the clarity of slides and oral communication. Questions on at least one paper will be included on the final exam. Papers 1) Zuend, S.; Coughlin, M.; Lalonde, M.; Jacobsen, E. Scaleable catalytic asymmetric Strecker syntheses of unnatural-amino acids. Nature 2009, 461(7266), 968-970. 2) Hamilton, G.; Kang, E.; Mba, M.; Toste, F. A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis. Science 2007, 317(5837), 496-499. 3) Unni, A.; Takenaka, N.; Yamamoto, H.; Rawal, V., Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels−Alder Reactions through Hydrogen Bonding. J Am Chem Soc 2005, 127(5), 1336-1337. 4) Savile, C. K.; Janey, J. M.; Mundorff, E. C.; Moore, J. C.; Tam, S.; Jarvis, W. R.; Colbeck, J. C.; Krebber, A.; Fleitz, F. J.; Brands, J.; Devine, P. N.; Huisman, G. W.; Hughrs, G. J. Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture. Science 2010, 329(5989), 305. 5) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones. J. Am. Chem. Soc. 2013, 135, 7442. 6) Furuya, T.; Strom, A.; Ritter, T., Silver-Mediated Fluorination of Functionalized Aryl Stannanes. J Am Chem Soc 2009, 131, 1662-1663. 7) He, J.; Li, S.; Deng, Y.; Fu, H.; Laforteza, B. N.; Spangler, J. E.; Homs, A.; Yu, J.-Q. Ligand-Controlled C(sp3)–H Arylation and Olefination in Syntheses of Unnatural Chiral α-Amino Acids. Science 2014, 343, 1216. 8) Han, S.; Miller, S. J. Asymmetric Catalysis at a Distance: Catalytic, Site-Selective Phosphorylation of Teicoplanin. J. Am. Chem. Soc. 2013, 135, 12414. 9) Zultanski, S. L.; Fu, G. C. Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings. J. Am. Chem. Soc. 2011, 133, 15362. 10) Mei, T.-S.; Patel, H. H.; Sigman, M. S. Enantioselective Construction of Remote Quaternary Stereocenters. Nature 2014, 508, 340. 11) Endo, K.; Grubbs, R. H. Chelated Ruthenium Catalysts for Z-Selective Olefin Metathesis. J. Am. Chem. Soc. 2011, 133, 8525. 12) Malcolmson, S. J.; Meek, S. J.; Sattely, E. S.; Schrock, R. R.; Hoveyda, A. H. A New Class of Chiral Catalysts for Enantioselective Alkene Metathesis. Nature 2008, 456, 933. 13) Hoye, T. R.; Baire, B; Niu, D.; Willoughby, P. H.; Woods, B. P. The Hexadehydro-Diels–Alder Reaction. Nature 2012, 490, 208. 14) Quasdorf, K.; Tian, X.; Garg, N., Cross-Coupling Reactions of Aryl Pivalates with Boronic Acids. J Am Chem Soc 2008, 130, 14422-14423. 15) Nicewicz, D.; MacMillan, D., Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes. Science 2008, 322, 77-80. 16) Burks, H.; Kliman, L.; Morken, J., Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration. J Am Chem Soc 2009, 131, 9134-9135. CHEM 633 Advanced Organic Chemistry: Physical Presentation Sign-Up Sheet Paper Zuend, Jacobsen. J. Am. Chem. Soc. 2007, 129, 15872. Blackmond. Angew. Chem. Int. Ed. 2005, 44, 4302. Harper, Sigman. Proc. Nat. Acad. Sci. 2011, 108, 2179. Shekhar, Ryberg, Hartwig, Mathew, Blackmond, Strieter, Buchwald. J. Am. Chem. Soc. 2006, 128, 3584. Byers, Jamison. J. Am. Chem. Soc. 2009, 131, 6383. Deprez, Sanford. J. Am. Chem. Soc. 2009, 131, 11234. Sun, Gorelsky, Stuart, Campeau, Fagnou. J. Org. Chem. 2010, 75, 8180. Lutz, Rathbun, Stevenson, Powell, Boman, Baxter, Zona, Johnson. J. Am. Chem. Soc. 2012, 134, 715. Presenter 1 Presenter 1