Evidence for a stepwise mechanism in formal hetero-Diels-Alder reactions of N-arylimines

Tetrahedron

Volumn 52, Issue 3, 1996, Pages 955-970

  Linkert, Frank ^a   Laschat, Sabine ^a   Kotila, Sirpa ^a   Fox, Thomas ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; INDOLIZINE DERIVATIVE; PYRROLIDINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

BETULACEAE;

EID: 0030021298     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00947-7     Document Type: Article

References (42)

1. For reviews on hetero-Diels-Alder reactions see: a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: New York, 1987, p. 35.
2. b) Weinreb, S. M. in Comprehensive Organic Synthesis, Trost, B. M. Ed., Pergamon Press: Oxford 1991, vol. 5, p. 401-449.
3. c) Boger, D. L. in Comprehensive Organic Synthesis, vol. 5, p. 451-512.
4. d) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087-3128.
5. e) Boger, D. L. Chem. Rev. 1986, 86, 781-793.
6. f) Asymmetric hetero-Diels-Alder reactions: Waldmann, H. Synthesis 1994, 535-551.
7. Some recent examples of imino-Diels-Alder reactions: a) Lock, R.; Waldmann, H. Liebigs Ann. Chem. 1994, 511-516 and refs. cited therein,
8. b) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1993, 58, 2068-2074.
9. c) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc. 1993, 115, 2248-2260.
10. d) Barluenga, J.; Tomas, M.; Ballesteros, A.; Gotor, V. J. Chem. Soc. Chem. Commun. 1989, 267-269.
11. e) Pfrengle, W.; Kunz, H. J. Org. Chem. 1993, 54, 4261-4263.
12. f) Kunz, H.; Pfrengle, W. Angew. Chem. Int. Ed. Engl. 1989, 28, 1067 -1068.
13. g) Wojciechowski, K. Tetrahedron 1993, 49, 7277-7286.
14. h) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801-804.
15. i) Mellor, J. M.; Merriman, G. D.; Riviere, P. Tetrahedron Lett. 1991, 32, 7103-7106.
16. j) Gregoire, P. J.; Mellor, J. M.; Merriman, G. D. Tetrahedron Lett. 1991, 32, 7099-7102.
17. k) Palacios, F.; Perez de Heredia, I.; Rubiales, G. Tetrahedron Lett. 1993, 34, 4377-4380.
18. Ab initio calculations: a) Bachrach, S. M.; Liu, M. J. Org. Chem. 1992, 57, 6736-6744.
19. b) Mc Carrick, M. A.; Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 1499-1500.
20. c) Tran Huu Dau, M. E.; Flament, J. P.; Lefour, J. M.; Riche, C.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 2343-2346.
21. Tietze, L. F.; Geissler, H.; Fennen, J.; Brumby, T.; Brand, S.; Schulz, G. J. Org. Chem. 1994, 59, 182-191. See also: Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. Engl. 1993, 31, 131-164.
22. Tietze, L. F.; Geissler, H.; Fennen, J.; Brumby, T.; Brand, S.; Schulz, G. J. Org. Chem. 1994, 59, 182-191. See also: Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. Engl. 1993, 31, 131-164.
23. Tietze, L. F.; Utecht, J. Chem. Ber. 1992, 125, 2259-2263.
24. Recent ab initio and semiempirical calculations on the Diels-Alder reaction of 1-aza-1,3-butadiene and ethene by Tietze et al. showed a preference for the stepwise mechanism: Tietze, L. F.; Fennen, J.; Geißler, H.; Schulz, G.; Anders, E. Liebigs Ann. Chem. 1995, 1681-1687.
25. a) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132.
26. b) Gregoire, P. J.; Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6133-6144.
27. For earlier work in this area see: Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858.
28. a) Linkert, F.; Laschat, S. Synlett 1994, 125-126.
29. b) Linkert, F.; Laschat, S.; Knickmeier, M. Liebigs Ann. Chem. 1995, 985-993.
30. a) Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Muehlbacher, M.; Poulter, C. D. J. Org. Chem. 1986, 57, 4768-4779.
31. b) Davisson, V. J.; Woodside, A. B.; Poulter, C. D. Methods Enzymol. 1984, 110, 130-144.
32. Biernacki, W.; Gdula, A. Synthesis 1979, 37-38.
33. Rodriguez-Avial Franke, L. R.; Wolf, H. Tetrahedron 1984, 40, 3491-3498.
34. Ali, F. E.; Bondinell, W. E.; Dandrige, P. A.; Frazee, J. S.; Garvey, E.; Girard, G. R.; Kaiser, C.; Ku, T. W.; Lafferty, J. J.; Moonsammy, G. I.; Oh, H. J.; Rush, J. A.; Setler, P. E.; Struger, O. D.; Venslavsky, J. W., Volpe, B. W.; Yunger, L. M.; Zirkle, C. L. J. Med. Chem. 1985, 28, 653-660.
35. Daniels, S. B.; Cooney, E.; Sofia, M. J.; Chakravarty, P. K.; Katzenellenbogen, J. A. J. Biol. Chem. 1983, 258, 15046-15053.
36. Lubell, W. D.; Jamison, T. F.; Rapoport, H. J. Org. Chem. 1990, 55, 3511-3522.
37. Dike, S. Y.; Mahaligau, K.; Kumar, A. Tetrahedron Lett. 1990, 31, 4641-4644.
38. Agami, C.; Couty, F.; Lin, J.; Mikaeloff, A.; Poursoulis, M. Tetrahedron 1993, 49, 7239-7250.
39. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
40. The chemical shift for C-12a (δ 55.2 ppm) of the all-irons compound 19a is in good agreement with the above mentioned data.
41. 2 = 0.154; diffractometer: Enraf-Nonius CAD4; programs used: SHELX-86, SHELX-93, SCHAKAL-92. Further details can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
42. 2 was also observed during isolation of melonine: Mehri, H.; Baassou, S.; Plat, M. J. Nat. Prod. 1991, 54, 372.