Density functional theory study of a Lewis acid catalyzed Diels-Alder reaction. The butadiene + acrolein paradigm

Journal of the American Chemical Society

Volumn 120, Issue 10, 1998, Pages 2415-2420

  Garcia J I ^a   Martinez Merino V ^b   Mayoral, J A ^a   Salvatella, L ^a,c  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b PUBLIC UNIVERSITY OF NAVARRE   (Spain)

^c NANCY UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; ACROLEIN;

ARTICLE; CALCULATION; CATALYST; CHEMICAL REACTION; CONFORMATION; CONTROLLED STUDY; ENERGY; ENZYME SPECIFICITY; NONHUMAN;

EID: 2642662490     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9722279     Document Type: Article

References (28)

1. Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1996.
2. Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127.
3. Yamabe, S.; Dai, T.; Minato, T. J. Am. Chem. Soc. 1995, 117, 10994.
4. Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, D.-Y. J. Org. Chem. 1995, 60, 8128.
5. González, J.; Sordo, T.; Sordo, J. A. J. Mol. Struct. (THEOCHEM) 1996, 358, 23.
6. Sbai, A.; Branchadell, V.; Ortuño, R. M.; Oliva, A. J. Org. Chem. 1997, 62, 3049.
7. García, J. I.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1996, 118, 11680.
8. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
9. (b) Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785.
10. (a) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036.
11. (b) Wiest, O.; Houk, K. N. Top. Cur. Chem., 1996, 183, 1 and references cited therein.
12. (a) Froese, R. D. J.; Humbel, S.; Morokuma, K. J. Phys. Chem. 1997, 101, 227.
13. (b) Jursic, B. S.; Zdravkovski, Z. J. Chem. Soc., Perkin Trans. 2 1995, 1223.
14. (c) Jursic, B. S. J. Org. Chem. 1995, 60, 4721.
15. GAUSSIAN 94 (Revision C.2 and D.3), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Latham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andrés, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; González, C.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 1995.
16. (a) González, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
17. (b) González, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
18. Loncharich, R. J.; Brown, F. W.; Houk, K. N. J. Org. Ghem. 1989, 54, 1129.
19. Kistiakowski, G. B.; Lacher, J. R. J. Am. Chem. Soc. 1936, 58, 123.
20. Inukai, T.; Kojima, T. J. Org. Chem. 1967, 32, 872.
21. Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1991, 113, 7430.
22. Ruiz-López, M. F.; Assfeld, X.; García, J. I.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1993, 115, 8780.
23. Jorgensen, W. L.; Lim, D.; Blake, J. F. J. Org. Chem. 1994, 59, 801.
24. García, J. I.; Mayoral, J. A.; Salvatella, L. Tetrahedron 1997, 53, 6057.
25. Jorgensen, W. L.; Lim, D.; Blake, J. F. J. Am. Chem. Soc. 1993, 115, 2936.
26. Froese, R. D. J.; Organ, M. G.; Goddard, J. D.; Stack, T. D. P.; Trost, B. M. J. Am. Chem. Soc. 1995, 117, 10931.
27. Beno, B. R.; Houk, K. N.; Singleton, D. A. J. Am. Chem. Soc. 1996, 118, 9984.
28. Singleton, D. A. J. Am. Chem. Soc. 1992, 114, 6563.