CHE535 2007 Running List of Assignments

Priority	Assignments
	[session 01] Review the Cahn, Ingold Prelog rules in an Organic Chemistry Textbook or click here      IF NEEDED ------------------------------
	Organic oxidation state: J. March, Advanced Organic Chemistry, third edition, chapter 19, p. 1048. Or see the index for oxidation and reduction or the relevant sections in other editions. ------------------------------
	[session 02] Ziegler, F. E. "The Thermal Aliphatic Claisen Rearrangement." Chem. Rev. 1988, 88, 1423.      Pay special attention to the Ireland Ester Claisen rearrangement. It is easier to apply. It will mean more when we talk about control of enolate stereochemistry.      ------------------------------
	Bennett, G. B. "The Claisen Rearrangement in Organic Synthesis." Synthesis 1977, 589. ------------------------------
	Blechert, S. "The Hetero-Cope Rearrangement in Organic Synthesis." Synthesis 1989, 71. ------------------------------
	1) Ciganek, E. (1984). "The Intramolecular Diels-Alder Reaction." Org. React. (N.Y.) 32: 1. 2) Roush, W. R. "Intramolecular Diels-Alder Reactions." In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5; pp 513.      Read/ scan to be able to do practice problem assignment 1. ------------------------------
	Erdik, E. "Copper(I)-Catalysed Reactions of Organolithiums and Grignard Reagents" Tetrahedron 1984, 40, 641. ------------------------------
	Yamamoto, Y. ; Yamamoto, H.Y.; Maruyama, K.; Ishihara, Y. J. Org. Chem. 1982, 47, 119-126. CuI, (R-Li or RMgX), BF3OEt2. ------------------------------
	Sutherland, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3; pp 341.      Read/ scan to be able to do practice problem assignment 2. ------------------------------
	[session 03] The Cubane System: Cole, T.W.; Eaton, P.E. J. Am. Chem. Soc. 1964, 86, 962-964.      This is a short communication that you should be able to cut through quickly after Session 3. It is important for you to start reading for comprehension at this level. With session 3 as a background you will be able to evaluate your level of understanding of other primary chemical literature with this paper as the standard. ------------------------------
	Wiberg, K. B. "The Concept of Strain in Organic Chemistry" Angew. Chem., Int. Ed. Engl. 1986, 25: 312. ------------------------------
	The Favorskii rearrangement || link 1||  link 2|| ------------------------------
	[session 04] Protecting Groups to Consider: You might use this section to scan for protecting groups when faced with an out-of-class assignment.     (1) protecting groups read: pp. 1-5. Gaze in awe and skip the other complex molecules discussed.     (2) protecting groups there are some links. the others you can look up further     (3) protecting groups wikipedia (surprisingly good!) ------------------------------
	Kozlowski, J. A. "Organocuprates in the Conjugate Addition Reaction." In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4; pp 169. ------------------------------
	[session 05] Synthesis of Cecropia-C18 juvenile hormone. The first synthesis that we considered session 5 is not assigned reading. (1) Corey, E.J.; Katzenellenbogen, J.A.; Gilman, N.W.; Roman S.A.; Erickson,B.W. "Stereospecific total synthesis of the dl-C18 Cecropia juvenile hormone" J. Am. Chem. Soc. 1968, 90, 5618-5620. (2) Henrick, C. A.; Schaub, F.; Siddall, J. B. "Stereoselective Synthesis of the C-18 Cecropia Juvenile Hormone " J. Am. Chem. Soc. 1972, 94, 5374-5378. (3) Still, W. C.; McDonald, J. H., III; Collum, D. B.; Mitra, A. "A Highly Stereoselective Synthesis Of The Cl8 Cecropia Juvenile Hormone" Tet. Lett. 1979, 20, 593. ------------------------------
	Mander, L. N. (1991). Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods. Comprehensive Organic Synthesis. B. M. Trost and I. Fleming. Oxford, Pergamon Press. 8: 489. Rabideau, P. W. and Z. Marcinow (1992). "The Birch Reduction of Aromatic Compounds." Org. React. (N.Y.) 42: 1-334. Birch, A. J. and D. H. Williamson (1976). "Homogeneous Hydrogenation Catalysts in Organic Synthesis." Org. React. (N.Y.) 24: 1. ------------------------------
	Stec, W.J. "Wadsworth-Emmons reaction revisited." Acc. Chem. Res. 1983, 16, 411 - 417. Li, A. H.; Dai, L. X.; Aggarwal, V. K. "Asymmetric ylide reactions: Epoxidation, cyclopropanation, aziridination, olefination, and rearrangement." Chem. Rev. 1997, 97, 2341-2372. Read the introduction then skip to p 2367 at the section Asymmetric Olefinations. Read to the end. ------------------------------
	Read/ scan above to be able to do practice problem assignment 3. ------------------------------
	[session 06] Read the following to reviews in Comprehensive Org. Syn. Read the introductions carefully. Pay attention to the stereochemical arguments. Scan the examples to get a feel for the chemistry. Caine, D. "Alkylations of Enols and Enolates." In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3; pp 1. ------------------------------
	Heathcock, C. H. "The Aldol Reaction: Group I and Group II Enolates." In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2; pp 181. ------------------------------
	[session 07] The Aldol Reaction Wikipedia ------------------------------
	Read/ scan, see notes, do practice problem assignment 4. ------------------------------
	END OF MATERIAL FOR THE MIDTERM EXAM ------------------------------
	Remit Problem Assignment One (Thurs March 22 2007) ------------------------------
	[session 08] hydroboration ------------------------------
	Smith, K.; Pelter, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8; pp 703. Skim this review to familiarize yourself with the chemsitry. What can hydroboration chemsitry accomplish synthetically with control of stereochemsitry. ------------------------------
	Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695-4712. Read for an appreciation of how the hydroboration chemistry changes under transition metal catalysis. ------------------------------
	Frohn, M.; Shi, Y. "Chiral ketone-catalyzed asymmetric epoxidation of olefins." Synthesis 2000, 1979-2000.  Read to understand this chemistry and the background issues. Diastereomeric transtion states are of different energies. Thus diastereomers are produced at different rates. This is the basis of asymmetric synthesis. ------------------------------
	Atom economy, wikipedia. ------------------------------
	On atom economy.  Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259-281. ------------------------------
	Sharpless asymmetric epoxidation, wikipedia. ------------------------------
	Sharpless asymmetric dihydroxylation, wikipedia. ------------------------------
	[session 09] Please Read:  Furber, M. "Alkynes.” In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Elsevier Science: Oxford, U.K., 1995; Vol. 1, pp 997-1086. ------------------------------
	Swaminathan, S.; Narayanan, K. V. "The Rupe and Meyer-Schuster Rearrangements." Chem. Rev. 1971, 71, 429. ------------------------------
	Read the Wikipedia blurb on the Robinson Annulation. Think about incorporating this reaction into your synthetic tool kit. Can you imagine reducing the alpa-beta unsaturated ketone to a cyclohexanone? What about completely defunctionalizing the ring to cyclohexane? Can you see the Robinson Retron in a simple cyclohexane ring fused to another cyclohexane ring? ------------------------------
	Read this review to familiarize yourself with the chemistry. Sonogashira, K. "Coupling Reactions Between sp2 and sp Carbon Centers." In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3; pp 521. ------------------------------
	Remit Problem Assignment Two (Thurs April 03 2007) ------------------------------
	[session 10] Read and Understand Synthesis of (+)-parviflorin” Hoye, T.R.; Ye, Z.  J. Am. Chem. Soc. 1996, 118, 1801-1802 .  ||local|| ------------------------------
	Remit Problem Assignment Three (Thurs April 27 2007, last day of class, or before) ------------------------------
	[session 11] Read and understand: http://en.wikipedia.org/wiki/Mitsunobu_reaction ------------------------------
	Read and understand why the phenol and not the alcohol is the nucleophile. "ADDP and PS-PPh3: an efficient Mitsunobu protocol for the preparation of pyridine ether PPAR agonists" Beilstein JOC. 2006, 2. 21. ------------------------------
	[session 12] Read Schultz' Synthesis of Longifolene. Scan through "Intramolecular Dipolar Cycloaddition Reactions of Azomethine Ylides" Chem. Rev. 2005, 105, 2765-2809. ------------------------------
	[session 13] Scan through "Expansion to Seven-Membered Rings" Tetrahedron 56 (2000) 4317. Pay attention to the abundance of carbene chemistry. ------------------------------
	[session 14] start here http://en.wikipedia.org/wiki/Wolff_rearrangement Checkout the rich chemistry and the many possibilities to trap intermediates in the Wolff Rearrangement. Gill, G. B. "The Wolff Rearrangement."In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 887. ------------------------------
	[session 15] READ Howard E. Zimmerman “Kinetic Protonation Of Enols, Enolates, And Analogues. The Stereochemistry Of Ketonization” Acc. Chem. Res. 1987, 20, 263-268. READ E. Vedejs, A. W. Kruger, N. Lee, S. T. Sakata, M. Stec, and E. Suna “Enantioselective Enolate Protonation with Chiral Anilines: Scope, Structural Requirements, and Mechanistic Implications” J. Am. Chem. Soc. 2000, 122, 4602-4607 NOW link the two phenomena together. Can you find a way to state how they are related? ------------------------------
	[session 16] Wikipedia on Pinacol. Pinacol Coupling      See the review sited in the notes. Pinacol Rearrangement      Can you plan syntheses based on this rearrangement? Se the review cited in the notes and practice looking at molecules with the aim to perform retrosynthesis based on the Pinacol rearrangement. ------------------------------
	Read the review of the asymmetric Stetter reaction. ------------------------------