Effect of Lewis acid catalysts on Diels-Alder and hetero-Diels-Alder cycloadditions sharing a common transition state

Journal of Organic Chemistry

Volumn 73, Issue 19, 2008, Pages 7472-7480

  Çelebi Ölçüm, Nihan ^a,b   Ess, Daniel H ^b   Aviyente, Viktorya ^a   Houk, K N ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BOGAZICI UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; ETHERS; OLEFINS; POTENTIAL ENERGY SURFACES; PROBABILITY DENSITY FUNCTION; QUANTUM CHEMISTRY;

BOND LENGTHS; BRANCHING RATIO; CLAISEN REARRANGEMENTS; CYCLOADDITION TRANSITION; CYCLOADDITIONS; CYCLOADDUCTS; CYCLOPENTADIENE; DENSITY FUNCTIONAL THEORY METHODS; DIELS-ALDER; ENERGY-BARRIER; HETERO-DIELS-ALDER; LEWIS ACID CATALYSTS; LEWIS ACIDS; NITROALKENES; PERISELECTIVITY; POTENTIAL-ENERGY SURFACE; RELATIVE POSITIONING; TRANSITION STATE; TRANSITION STATES;

POTENTIAL ENERGY;

LEWIS ACID; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLAISEN CONDENSATION; CLAISEN REARRANGEMENT; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; HEAT TREATMENT; PHASE TRANSITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SURFACE PROPERTY;

CATALYSIS; COMPUTER SIMULATION; CYCLOPENTANES; MODELS, CHEMICAL; MODELS, MOLECULAR; THERMODYNAMICS;

EID: 53049104386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801076t     Document Type: Article

References (45)

1. (a) Kraka, E. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; Wiley: New York, 1998; Vol. 4, p 2445.
2. (b) Carpenter, B. K. In Reactive Intermediate Chemisty; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; pp 925-960.
3. (c) Wenthold, P. G.; Hrovat, D. A.; Borden, W. T.; Lineberger, W. C. Science 1996, 272, 1456-1459.
4. Ess, D. H.; Wheeler, S. E.; Iafe, R. G.; Xu, L.; Çelebi- Ölçüm, N.; Houk, K. N. Angew. Chem. In press. This review article provides the most complete list of reactions with bifurcating potential energy surfaces.
5. Singleton, D. A.; Hang, C.; Szymanski, M. J.; Meyer, M. P.; Leach, A. G.; Kuwata, K. T.; Chen, J. S.; Greer, A.; Foote, C. S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 1319-1328.
6. (a) Valtazanos, P.; Ruedenberg, K. Theor. Chim. Acta 1986, 69, 281-307.
7. (b) Xantheas, S.; Elbert, S. T.; Ruedenberg, K. Theor. Chim. Acta 1991, 78, 365-395.
8. (c) Valtazanos, P.; Ruedenberg, K. Theor. Chim. Acta 1991, 78, 397-416.
9. (d) Basilevsky, M. V. Chem. Phys. 1977, 24, 81-89.
10. (e) Quapp, W.; Hirsch, M.; Heidrich, D. Theor. Chem. Acc. 1998, 100, 285-299.
11. (f) Quapp, W.; Hirsch, M.; Heidrich, D. Theor. Chem. Acc. 2000, 105, 145-155.
12. (g) Quapp, W. J. Theor. Comp. Chem. 2003, 2, 385-417.
13. (h) Quapp, W. J. Mol. Struct. 2004, 695-696, 95-101.
14. (i) Quapp, W.; Hirsch, M.; Heidrich, D. Theor. Chem. Acc. 2004, 112, 40-51.
15. See ref 2 for the distinction between reaction pathway, minimum energy pathway, intrinsic reaction coordinate, and valley-ridge inflection, and their relationship to bifurcations. Here we use minimum energy pathway and intrinsic reaction coordinate synonymously.
16. (a) Sun, L.; Song, K.; Hase, W. L. Science 2002, 296, 875-878.
17. (b) Mann, D. J. J. Am. Chem. Soc. 2002, 124, 3208-3209.
18. (c) Lopez, J. G.; Vayner, G.; Lourderaj, U.; Addepalli, S. V.; Kato, S.; de Jong, W. A.; Windras, T. L.; Hase, W. L. J. Am. Chem. Soc. 2007, 129, 9976-9985.
19. Caramella, P.; Quadrelli, P.; Toma, L. J. Am. Chem. Soc. 2002, 124, 1130-1131.
20. This does not account for possible rearrangements that may also occur.
21. (a) Toma, L.; Romano, S.; Quadrelli, P.; Caramella, P. Tetrahedron Lett. 2001, 42, 5077-5080.
22. (b) Quadrelli, P.; Romano, S.; Toma, L.; Caramella, P. Tetrahedron Lett. 2002, 43, 8785-8789.
23. (c) Quadrelli, P.; Romano, S.; Toma, L.; Caramella, P. J. Org. Chem. 2003, 68, 6035-6038.
24. (d) Dinadayalane, T. C.; Sastry, G. N. Organometallics 2003, 22, 5526-5533.
25. Leach, A. G.; Goldstein, E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 8330-8339.
26. Limanto, J.; Khuong, K. S.; Houk, K. N.; Snapper, M. L. J. Am. Chem. Soc. 2003, 125, 16310-16321.
27. Dinadayalane, T. C.; Gayatri, G.; Sastry, G. N.; Leszczynski, J. J. Phys. Chem. A 2005, 109, 9310-9323.
28. Ussing, B. R.; Hang, C.; Singleton, D. A. J. Am. Chem. Soc. 2006, 128, 7594-7607.
29. (a) Yamabe, S.; Dai, T.; Minato, T.; Machiguchi, T.; Hasegawa, T. J. Am. Chem. Soc. 1996, 118, 6518-6519.
30. (b) Yamabe, S.; Minato, T. J. Org. Chem. 2000, 65, 1830-1841.
31. Hanessian, S.; Compain, P. Tetrahedron 2002, 58, 6521-6529.
32. Denmark, S. E.; Kesler, B. S.; Moon, Y.-C. J. Org. Chem. 1992, 57, 4912-4924, and references cited therein.
33. (a) Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1998, 120, 4895-4896.
34. (b) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 1999, 122, 1635-1649.
35. Çelebi-Ölçüm, N.; Ess, D. H.; Aviyente, V.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 4528-4529.
36. Frisch, M. J.; et al. Gaussian 03, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
37. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
38. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
39. (a) Yamaguchi, K.; Jensen, F.; Dorigo, A.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537-542.
40. (b) Yamanaka, S.; Kawakami, T.; Nagao, H.; Yamaguchi, K. Chem. Phys. Lett. 1994, 231, 25-33.
41. (a) Hoffmann, R.; Woodward, R. B. J. Am. Chem. Soc. 1965, 87, 4388-4389.
42. (b) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970.
43. (c) Salem, L. J. Am. Chem. Soc. 1968, 90, 553-566.
44. (d) Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127-4133.
45. Telan, L. A.; Poon, C.-D.; Evans, S. A., Jr J. Org. Chem. 1996, 61, 7455-7462.