Exo-Selective Diels-Alder Reactions of Vinylazepines. Origin of Divergent Stereoselectivity in Diels-Alder Reactions of Vinylazepines, Vinylpiperideines, and Vinylcycloalkenes

Journal of Organic Chemistry

Volumn 68, Issue 23, 2003, Pages 8991-8995

  Boren, Brant ^a   Hirschi, Jennifer S ^a   Reibenspies, Joseph H ^a   Tallant, Matthew D ^a   Singleton, Daniel A ^a   Sulikowski, Gary A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTIONS;

ISOMERS; REACTION KINETICS; STEREOCHEMISTRY; X RAY ANALYSIS;

ORGANIC COMPOUNDS;

ALKADIENE; AZEPINE DERIVATIVE; CYCLOALKENE; MALEIMIDE DERIVATIVE; N PHENYLMALEIMIDE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLAZEPINE DERIVATIVE; VINYLPIPERIDEINE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; EPIMERIZATION; MATHEMATICAL MODEL; PREDICTION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; X RAY ANALYSIS;

AZEPINES; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 0242576150     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034462h     Document Type: Article

References (46)

1. (a) Gotz, M.; Edwards, O. E. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. IX, pp 545-551.
2. (b) Gotz, M.; Strunz, G. M. In Alkaloids: MTP International Review of Sciences; Wiesner, K., Ed.; Butterworth: London, 1973; Series One, Vol. IX, pp 143-160.
3. (a) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236-6240.
4. (b) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840-3849.
5. (c) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106-11112.
6. (d) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904-906,
7. (e) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem.-Eur. J. 2001, 7, 4107-4116,
8. During the preparation of this manuscript two syntheses of stenine have appeared that use a Diels-Alder reaction as a key step: (a) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515-1517.
9. (b) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316-4318.
10. Du Ha, J.; Kang, C. H.; Belmore, K. A.; Cha, J. K. J. Org. Chem. 1998, 63, 3810-3811.
11. Occhiato, E. G.; Trabocchi, A.; Guama, A. Org. Lett. 2000, 2, 1241-1242.
12. (a) Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 8131-8140.
13. (b) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803-805.
14. (a) Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656-2657.
15. (b) Okita, T.; Isobe, M. Synlett 1994, 589-590.
16. (c) Okita, T.; Isobe, M. Tetrahedron 1995, 51, 3737-3744.
17. (d) Tsushima, K.; Hirade, T.; Hasegawa, H.; Murai, A. Chem. Lett. 1995, 801-802.
18. (e) Occhiato, E. G.; Trabocchi, A.; Guarna, A. J. Org. Chem. 2001, 66, 2459-2465.
19. (f) Nicolaou, K. C.; Shi, G.-Q.; Namoto, K.; Bernal, F. Chem. Commun. 1998, 1757-1758.
20. Enecarbamate 4 was prepared from Boc-protected homopiperidine by electrochemical methoxylation followed by acid-catalyzed elimination of methanol. Cf. Nyberg, K. Synthesis 1976, 545-546. For an alternative preparation starting from carporlactam see ref 9b.
21. (a) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056-9062.
22. (b) Wilkinson, T. J.; Stehle, N. W.; Beak, P. Org. Lett. 2000, 2, 155-158.
23. Structure determination of 14 is described in the Supporting Information.
24. (a) Fotiadu, F.; Pardigon, O.; Buono, G.; Le Corre, M.; Hercouet, A. Tetrahedron Lett. 1999, 40, 867-870.
25. (b) Barluenga, J.; Canteli, R.-M.; Florez, J.; Garcia-Granda, S.; Gutierrez-Rodriguez, A.; Martin, E. J. Am. Chem. Soc. 1998, 120, 2514.
26. (c) Roush, W. R.; Koyama, K. Tetrahedron Lett. 1992, 33, 6227.
27. (d) Roush, W. R.; Reilly, M. L.; Koyama, K.; Brown, B. B. J. Org. Chem. 1997, 62, 8708.
28. (e) Pyne, S. G.; Dikic, B.; Gordon, P. A.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 46, 73-81.
29. (a) Kobuke, Y.; Fueno, T.; Furukawa, J. J. Am. Chem. Soc. 1970, 92, 6548-6553.
30. (b) Essers, M.; Wibbeling, B.; Haufe, G. Tetrahedron Lett. 2001, 42, 5429-5433.
31. (c) Maruoka, K.; Imoto, H.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 12115-12116.
32. (a) Powers, T. S.; Jiang, W.; Su, J.; Wulff, W. D.; Waltermire, B. E.; Rheingold, A. L. J. Am. Chem. Soc. 1997, 119, 6438-6439.
33. (b) Weyershausen, B.; Nieger, M.; Doetz, K. H. J. Org. Chem. 1999, 64, 4206.
34. (c) Sabat, M.; Reynolds, K. A.; Finn, M. G. Organometallics 1994, 13, 2084-2087.
35. Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537-562.
36. Ge, M.; Stoltz, B. M.; Corey, E. J. Org. Lett. 2000, 2, 1927-1929.
37. Yoon, T.; Danishefsky, S. J.; de Gala, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 853-855.
38. (a) Rosillo, M.; Casarrubios, L.; Dominguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2001, 42, 7029-7031.
39. (b) Schuster, T.; Kurz, M.; Göbel, M. W. J. Org. Chem. 2000, 65, 1697-1701.
40. (c) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Bruno, G.; Caruso, F. ; Giannetto, P. Tetrahedron: Asymmetry 2001, 12, 2901-2908.
41. Beno, B. R.; Houk, K. N.; Singleton, D. A. J. Am. Chem. Soc. 1996, 118, 9984-9985.
42. Hendrickson, J. B. J. Am. Chem. Soc. 1967, 89, 7036-7043.
43. A reviewer was concerned that the difference between experimental reaction with 19 and the calculational model 20 was too great. We have carried out calculations on the much more closely analogous reaction shown below (see the Supporting Information). As with the simpler model, the exo transition structure is correctly favored, in this case by 0.75 kcal/mol.
44. Jones, G. A.; Paddon-Row, M. N.; Sherburn, M. S.; Turner, C. I. Org. Lett. 2002, 4, 3789-3792.
45. House, H. O.; Tefertiller, B. A.; Olmstead, H. D. J. Org. Chem. 1968, 33, 935-942 House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 1000-1003.
46. House, H. O.; Tefertiller, B. A.; Olmstead, H. D. J. Org. Chem. 1968, 33, 935-942 House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 1000-1003.