Lewis acid-catalyzed tandem Diels-Alder reaction/retro-Claisen rearrangement as an equivalent of the inverse electron demand hetero Diels-Alder reaction

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6680-6684

  Davies, Huw M L ^a   Dai, Xing ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; ORGANIC ACIDS;

CYCLOPENTADIENE; HETERO DIELS-ALDER REACTION (HDA); LEWIS ACID;

REACTION KINETICS;

ALDEHYDE; CYCLOPENTADIENE DERIVATIVE; LEWIS ACID;

ARTICLE; CATALYSIS; CLAISEN CONDENSATION; CYCLOADDITION; DIELS ALDER REACTION; ELECTRON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 23644461386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050821s     Document Type: Article

References (40)

1. (a) Tietze, L. F.; Kettschau, G.; Gewart, J. A.; Schuffenhauer, A. Curr. Org. Chem. 1998, 2, 19.
2. (b) Tietze, L.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1.
3. (c) Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 451-512.
4. (d) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987.
5. Representative examples: (a) Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5, 2563.
6. (b) Phorboxazole: Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126.
7. (c) Altohyrtin: Kobayashi, M.; Aoki, S.; Kitigawa, I. Tetrahedron Lett. 1994, 35, 1243.
8. (d) Miyakolide: Higa, T.; Tanaka, J.; Komesu, M.; Gravalos, D. C.; Puentes, J. L. F.; Bernardinelli, G.; Jefford, C. W. J. Am. Chem. Soc. 1992, 114, 7587.
9. (e) Zincophorin: Brooks, H. A.; Gardner, D.; Poyser, J. P.; King, T. K. J. Antibiot. 1984, 37, 1501.
10. (f) Bryostatin 1: Pettit, G. R.; Herald, C. L.; Doubek, D. L.; Herald, D. L. J. Am. Chem. Soc. 1982, 104, 6846.
11. (g) Palytoxin: Cha, J. K.; Christ, W. J.; Finan, J. M.; Fujioka, H.; Kishi, Y.; Klein, L. L.; Ko, S. S.; Leder, J.; McWhorter, W. W.; Pfaff, K.-P.; Yonaga, M.; Uemura, D.; Hirata, Y. J. Am. Chem. Soc. 1982, 104, 7369.
12. (h) X-537A (Lasalocid A): Westley, J. W.; Evans, R. H.; Williams, T.; Stempel, A. Chem. Commun. 1970, 71.
13. (i) Monensin: Agtarap, A.; Chamberlin, J. W.; Pinkerton, M.; Steinrauf, L. J. Am. Chem. Soc. 1967, 89, 5737.
14. (a) Evans, D. A.; Olhava, E. J.; Johnson, J. S.; Janey, J. M. Angew. Chem., Int. Ed. 1998, 37, 3372.
15. (b) Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1998, 120, 4895.
16. (c) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635.
17. (d) Thorhauge, J.; Johannsen, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 2404.
18. (e) Audrain, H.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487.
19. (f) Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498.
20. (g) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 9, 1637.
21. (h) Wada, E.; Pei, W.; Yasuoka, H.; Chin, U.; Kanemasa, S. Tetrahedron 1996, 52, 1205.
22. (i) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059.
23. (a) Hanessian, S.; Compain, P. Tetrahedron 2002, 58, 6521.
24. (b) Arimori, S.; Kouno, R.; Okauchi, T.; Minami, T. J. Org. Chem. 2002, 67, 7303.
25. (c) Boeckman, R. K., Jr.; Flann, C. J.; Poss, K. M. J. Am. Chem. Soc. 1985, 107, 4359.
26. (d) Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098.
27. For reviews of the Claisen rearrangement and tandem cycloadditions, see: (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423.
28. (b) Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 1461.
29. (c) Neuschutz, K.; Velker, J.; Neier, R. Synthesis 1998, 227.
30. (a) Davies, H. M. L.; Dai, X. J. Am. Chem. Soc. 2004, 126, 2692.
31. (b) Niess, B.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. 2005, 44, 26.
32. Examples of cyclopentadiene behaving as dienophile: (a) Corey, E. J.; Munroe, J. E. J. Am. Chem. Soc. 1982, 104, 6129.
33. (b) Ismail, Z. M.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1982, 21, 859.
34. (c) Dvorak, D.; Arnold, Z. Tetrahedron Lett. 1982, 23, 4401.
35. (d) Nenajdenko, V. G.; Statsuk, A. V.; Balenkova, E. S. Tetrahedron 2000, 56, 6549.
36. 1b, 1c, 1d, and 1l were synthesized according to literature procedures: (a) Laitalainen, T.; Kuronen, P.; Hesso, A. Org. Prep. Proced. Int. 1993, 25, 597.
37. (b) Takano, S.; Inomata, K.; Samizu, K.; Tomita, S.; Yanase, M.; Suzuki, M.; Iwabuchi, Y.; Takumichi, S.; Ogasawara, K. Chem. Lett. 1989, 1283. 1d must be reacted immediately because it is very prone to dimerize.
38. 1f, 1h, and 1i were synthesized according to a literature procedure: Kim, J.-K.; Kulawiec, R. J. J. Org. Chem. 1996, 61, 7656.
39. Song, Z.; Beak, P. J. Am. Chem. Soc. 1990, 112, 8126.
40. The product 41 was refluxed in toluene for 24 h. There was no retro-Claisen rearrangement, and the starting material was recovered.