WOSYPROSS - Topic Summary & Assignments

Topic for December 15, 2009, WOSYPROSS session: 7. Carboxylic Compounds (for assigned reading, please refer to CHVRN 1301 posting). The problem set will be prepared by Marija M.

Topic for December 8, 2009, WOSYPROSS session: 6. Nucleophilic Substitutions on the Carboxyl Carbon (for assigned reading, please refer to CHVRN 1301 posting). The problem set will be prepared by Filip P.

Topic for December 1, 2009, WOSYPROSS session: 5. Aromatic Substitutions (for assigned reading, please refer to CHVRN 1301 posting). The problem set will be prepared by Junyan H.

Topic for November 24, 2009, WOSYPROSS session: 4. Beta Eliminations (for assigned reading, please refer to CHVRN 1301 posting). The problem set will be prepared by Chad H.

Topic for November 10, 2009, WOSYPROSS session: 3. Electrophilic Additions (for assigned reading, please refer to CHVRN 1301 posting). The problem set will be prepared by Nolan G.

Topic for November 3, 2009, WOSYPROSS session: 2. Nucleophilic Substitutions (for assigned reading, please refer to CHVRN 1301 posting). The problem set will be prepared by Adam H.

Topic for October 17, 2009, WOSYPROSS session: 1. Radicals (for assigned reading, please refer to CHVRN 1301 posting). The problem set will be prepared by John M.

 

Topic for January 31, 2009, MechOM session: Heterocyclic Chemistry

For assigned problems, click here.

 

Topic for May 3, 2008, MechOM session: Stereoelectronics and Conformational Analysis

For recommended reading, click here.

 

Topic for June 30, 2007, MechOM session: Physical Organic Chemistry - Organic Reaction Mechanisms Part I

Carey & Sundberg, Advanced Organic Chemistry, Part A: Chapter 4.

 

Topic for March 24, 2007, MechOM session: Radical Reactions

Reviews: Curran, D. P. In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Ed.; Pergamon Press: Oxford, 1991; Vol. 4; pp 715. Sibi, M. P.; Manyem, S.; Zimmerman, J., "Enantioselective radical processes." Chem. Rev. 2003, 103, 3263-3295.

 

Topic for December 9, 2006, MechOM session: Fragmentation Reactions

Reference: Weyerstahl, P.; Marschall, H., Fragmentation Reactions. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Pergamon Press: Oxford, 1991; Vol. 6, p 1041. [pdf]

 

Topic for June 17, 2006, MechOM session: Cyclopropanation

References: (a) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B., "Stereoselective cyclopropanation reactions." Chem. Rev. 2003, 103, 977-1050. (b) Dolbier, W. R., Jr.; Battiste, M. A., "Structure, synthesis, and chemical reactions of fluorinated cyclopropanes and cyclopropenes." Chem. Rev. 2003, 103, 1071-1098. (c) Donaldson, W. A., "Synthesis of cyclopropane containing natural products." Tetrahedron 2001, 57, 8589-8628.

 

Topic for March 25, 2006, MechOM session: Allylation/Crotylation

References: (a) Chemler, S. R.; Roush, W. R., "Stereochemistry of the allylation and crotylation reactions of a-methyl-b-hydroxy aldehydes with allyl- and crotyltrifluorosilanes. Synthesis of anti,anti-dipropionate stereotriads and stereodivergent pathways for the reactions with 2,3-anti- and 2,3-syn-a-methyl-b-hydroxy aldehydes." J. Org. Chem. 2003, 68, 1319-1333. (b) Denmark, S. E.; Fu, J., "Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones." Chem. Rev. 2003, 103, 2763-2793. (c) Arefolov, A.; Panek, J. S., "Crotylsilane reagents in the synthesis of complex polyketide natural products: Total synthesis of (+)-discodermolide." J. Am. Chem. Soc. 2005, 127, 5596-5603.

 

Topic for December 3, 2005, MechOM session: Sophomore Organic Chemistry or How Sweet It Was!

References: The Vollhardt/Schore Textbook

 

Topic for July 23, 2005, MechOM session: Organocopper Chemistry

References:

Murphy, M. D.; Ogle, C. A.; Bertz, S. H., "Opening the black box': Oscillations in organocuprate conjugate addition reactions." Chem. Commun.2005, 854-856.

Bertz, S. H.; Human, J.; Ogle, C. A.; Seagle, P., "Subtle factors are important: Radical formation and transmetallation in reactions of butyl cuprates with cyclohexyl iodide." Org. Biomol. Chem.2005, 3, 392-394.

Yamanaka, M.; Kato, S.; Nakamura, E., "Mechanism and regioselectivity of reductive elimination of pi-allylcopper (III) intermediates." J. Am. Chem. Soc.2004, 126, 6287-6293.

Nakamura, E.; Yamanaka, M.; Mori, S., "Complexation of Lewis acid with trialkylcopperi(III): On the origin of BF3-acceleration of cuprate conjugate addition." J. Am. Chem. Soc.2000, 122, 1826-1827.

Nakamura, E.; Mori, S., "Wherefore art thou copper? Structures and reaction mechanisms of organocuprate clusters in organic chemistry." Angew. Chem. Int. Ed.2000, 39, 3750-3771.

Krause, N., "New results regarding the structure and reactivity of cyanocuprates - the end of an old controversy." Angew. Chem. Int. Ed.1999, 38, 79.

Kingsbury, C. L.; Smith, R. A. J., "Some observations on the mechanism of diorganocuprate 1,4-addition reactions with a,b-unsaturated ketones: Effects of diethyl ether in reactions of butylcoppers in toluene." J. Org. Chem.1997, 62, 4629-4634.

Lipshutz, B. H.; James, B., "New 1H and 13C Nmr spectral data on "higher order" cyanocuprates. If the cyano ligand is not on copper, then where is it?" J. Org. Chem.1994, 59, 7585-7587.

Lipshutz, B. H.; Sharma, S.; Ellsworth, E. L., "Higher order cyanocuprates R2Cu(CN)Li2: Discrete reagents or lower order lithium cyanide (LiCN) modified Gilman cuprates?" J. Am. Chem. Soc.1990, 112, 4032-4034.

Corey, E. J.; Hannon, F. J., "A possible transition state assembly for highly diastereoselective conjugate addition reactions of lithium dimethylcuprate with a,b-enones." Tetrahedron Lett.1990, 31, 1393-1396.

Corey, E. J.; Boaz, N. W., "Evidence for a reversible d,p*-complexation, b-cupration sequence in the conjugate addition reaction of gilman reagents with a,b-enones." Tetrahedron Lett.1985, 26, 6015.

Corey, E. J.; Boaz, N. W., "d-orbital stereoelectronic control of the stereochemistry of SN2' displacements by organocuprate reagents." Tetrahedron Lett.1984, 25, 3063-3066.

 

 

Topic for March 12, 2005, MechOM session: Woodward-Hoffmann Rules

References:

- David, C. W., "Revisiting Woodward-Hoffmann Rules." J. Chem. Ed. 1999, 76, 999-1001. (pdf)

- Patterson, R. T., "An improved interpretation of the Woodward-Hoffmann rules." J. Chem. Ed. 1999, 76, 1002-1007. (pdf)

- Dolbier, W. R., Jr.; Koroniak, H.; Houk, K. N.; Sheu, C., "Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions." Accounts of Chemical Research 1996, 29, 471-477. (pdf)

- DePuy, C. H., "Cyclopropanols." Acc. Chem. Res. 1968, 1, 33-41. (pdf)

- Woodward, R. B.; Hoffmann, R., "Conservation of orbital symmetry." Angewandte Chemie, International Edition in English 1969, 8, 781-853. (pdf)

 

Topic for December 11, 2004, MechOM session: Stereochemistry

References:

- Basic Organic Stereochemistry by Ernest L. Eliel, Samuel H. Wilen, Michael P. Doyle, Wiley 2001.

- Mikami, K.; Shimizu, M.; Zhang, H. C.; Maryanoff, B. E., "Acyclic stereocontrol between remote atom centers via intramolecular and intermolecular stereo-communication." Tetrahedron 2001, 57, 2917-2951.

- Hoffmann, R. W., "Conformation design of open-chain compounds." Angew. Chem., Int. Ed. Engl. 2000, 39, 2055-2070.

- Gung, B. W., "Diastereofacial selection in nucleophilic additions to unsymmetrically substituted trigonal carbons." Tetrahedron 1996, 52, 5263-5301.

 

Topic for August 28, 2004, MechOM session: Organometallics

References:

  1. Siu, T.; Cox, C. D.; Danishefsky, S. J., "Total synthesis of lactonamycinone." Angew. Chem. Int. Ed. 2003, 42, 5629-5634.
  2. Paleo, M. R.; Calaza, M. I.; Grana, P.; Sardina, F. J., "Stanna-brook rearrangement of carboxylic acid derivatives. Synthetic utility and mechanistic studies." Org. Lett. 2004, 6, 1061-1063.
  3. Calaza, M. I.; Paleo, M. R.; Sardina, F. J., "Application of baldwin's rules for the preparation of stable, β-leaving group-bearing organolithium compounds." J. Am. Chem. Soc. 2001, 123, 2095-2060.
  4. Jamieson, A. G.; Sutherland, A.; Willis, C. L., "The first enantioselective synthesis of the amino acid, (2s,3s,4r)-g-hydroxyisoleucine using a palladium(ii) catalysed 3,3-sigmatropic rearrangement." Org. Biomol. Chem. 2004, 2, 808-809.
  5. Gandon, V.; Bertus, P.; Szymoniak, J., "Zirconium-catalyzed ethylmagnesiation of imines - scope and mechanism." Eur. J. Org. Chem. 2001, 3677-3682.
  6. Kwan, M. L.; Yeung, C. W.; Breno, K. L.; Doxsee, K. M., "Stereoselective one-pot synthesis of vinylsilanes from aromatic aldehydes." Tetrahedron Lett. 2001, 42, 1411-1414.
  7. Hoffman, R. W.; Hölzer, B., "Concerted and stepwise grignard additions, probed with a chiral grignard reagent." Chem. Commun. 2001, 491-492.
  8. Murakami, M.; Itahashi, T.; Ito, Y., "Catalyzed intramolecular olefin insertion into a carbon-carbon single bond." J. Am. Chem. Soc. 2002, 124, 13976-13977.
  9. Molander, G. A.; Le Huérou, Y.; Brown, G. A., "Sequenced reactions with samarium(ii) iodide. Sequential intramolecular barbier cyclization/grob fragmentation for the synthesis of medium-sized carbocycles." J. Org. Chem. 2001, 66, 4511-4516.
  10. Wipf, P.; Aslan, D. C., "Synthesis of bicyclic ortho esters by epoxy ester rearrangements and study of their ring opening reactions." J. Org. Chem. 2001, 66, 337-343.
  11. Nakamura, E.; Mori, S., "Wherefore art thou copper? Structures and reaction mechanisms of organocuprate clusters in organic chemistry." Angew. Chem. Int. Ed. 2000, 39, 3750-3771.
  12. Sanford, M. S.; Love, J. A.; Grubbs, R. H., "Mechanism and activity of ruthenium olefin metathesis catalysts." J. Am. Chem. Soc. 2001, 123, 6543-6554.
  13. Davies, H. M.; Stafford, D. G.; Doan, B. D.; Houser, J. H., "Tandem asymmetric cyclopropanation/cope rearrangement. A highly diastereoselective and enantioselective method for the construction of 1,4-cycloheptadienes." J. Am. Chem. Soc. 1998, 120, 3326.
  14. Yang, D.; Li, J.-H.; Gao, Q.; Yan, Y.-L., "Lanthanide triflate-promoted palladium-catalyzed cyclization of alkenyl b-keto esters and amides." Org. Lett. 2003, 5, 2869-2871.
  15. Liu, P.; Jacobsen, E. N., "Total synthesis of (+)-ambruticin." J. Am. Chem. Soc. 2001, 123, 10772-10773.
  16. Lampropoulou, M.; Herrmann, R.; Wagner, G., "Novel platinum-catalysed cascade reactions: Cyclisation, ring expansion and 1,2-oxygen shift reaction of a camphor-derived diyne." Tetrahedron 2004, 60, 4635-4643.
  17. Mamane, V.; Gress, T.; Krause, H.; Fuerstner, A., "Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes." J. Am. Chem. Soc. 2004, 126, 8654-8655.
  18. Yamago, S.; Miyazoe, H.; Nakayama, T.; Miyoshi, M.; Yoshida, J., "A diversity-oriented synthesis of a-amino acid derivatives by a silyltelluride-mediated radical coupling reaction of imines and isonitriles." Angew. Chem. Int. Ed. 2003, 42, 117-120.

 

Topic for May 8, 2004, MechOM session: Applications of name reactions in natural product synthesis.

References:

  1. Synlett 1995, 941
  2. JCS PT1 2002, 1574
  3. THL 2002, 43, 2347
  4. JCSPT1 1987, 2829
  5. BCSJ 1995, 68, 2393
  6. TH 1995, 51, 5099
  7. CC 1997, 1491
  8. JACS 2001, 123, 10942
  9. OL 2001, 3, 1925
  10. TH 1999, 55, 5129
  11. OL 2002, 4, 1031
  12. JACS 2000, 122, 8071
  13. JOC 1993, 58, 4756
  14. JOC 1975, 40, 1521
  15. JACS 1988, 110, 3693
  16. JACS 1998, 120, 8305
  17. JOC 1992, 57, 7052
  18. TL 2001, 42, 4779

 

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