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
Nov 5, 5pm
Choose your paper. You must note your choice on the sign-up Google doc.
Link
to
the
Google
doc:
https://docs.google.com/spreadsheets/d/1KOVdgvx5EvaP1UpPfq9pO95hWwPGp
AJPtpJGrSKXytw/edit?usp=sharing
Thurs, Dec 3, 5pm
Presentations emailed to Mary. Mary will compile the presentations and email all of them to
the class by Fri, 12/4, 5pm.
Sat, Dec 5, 9am–?
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, Dec 5.
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.
17) J. C. Tellis, D. N. Primer, G. A. Molander "Single-electron Transmetalation in Organoboron Cross-coupling
by Photoredox/Nickel Dual Catalysis" Science 345, 433–436.
18) Worthy, A.D.; Joe, C.L.; Lightburn, T.E.; Tan, K. L."Application of a Chiral Scaffolding Ligand in Catalytic
Enantioselective Hydroformylation" J. Am. Chem. Soc. 2010, 132, 14757.
19) Llaveria, J.; Leonori, D.; Aggarwal, V. K. "Stereospecific Coupling of Boronic Esters with N-Heteroaromatic
Compounds" J. Am. Chem. Soc. 2015, 137, 10958–10961.
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