Convenient synthesis of heterobicycles by domino Heck-Diels-Alder reactions

European Journal of Organic Chemistry

Volumn , Issue 9, 2001, Pages 1673-1680

  Bhat, Laxminarayan ^a   Steinig, Arno G ^a   Appelbe, Ruth ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Diels Alder reaction; Heck reaction, intramolecular; Hexahydro 1H 2 pyrindines; Hexahydrobenzo c furans; Tetrahydroisoindolin 1 ones; Tetrahydroisoindolines

Indexed keywords

AMIDE; AMINE; ETHER DERIVATIVE; FUSED HETEROCYCLIC RINGS; ISOBENZOFURAN DERIVATIVE; ISOINDOLE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0035031052     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200105)2001:9<1673::AID-EJOC1673>3.0.CO;2-G     Document Type: Article

References (47)

1. [1a] L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
2. [1b] H. Waldmann, Domino Reactions in Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, p. 193 ff.
3. [1c] L. F. Tietze, U. Beifuß, Angew. Chem. 1993, 105, 137-170;
4. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-164.
5. [1d] D. P. Curran, in: Comprehensive Organic Synthesis, vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, p. 779-831.
6. [2a] B. B. Snider, N. H. Vo, B. M. Foxman, J. Org. Chem. 1993, 58, 7228-7237 and references therein.
7. [2b] N. Iwasawa, M. Funahashi, S. Hayakawa, K. Narasaka, Chem. Lett. 1993, 545-548.
8. [2c] A. Ali, D. C. Harrowven, G. Pattenden, Tetrahedron Lett. 1992, 33, 2851-2854.
9. [2d] R. Grigg, P. Kennewell, A. J. Teasdale, Tetrahedron Lett. 1992, 33, 7789-7792 and references therein.
10. [2e] D. Batty, D. Crich, J. Chem. Soc., Perkin Trans. 1 1992, 3205-3209 and references therein.
11. [2f] B. M. Trost, Y. Shi, J. Am. Chem. Soc. 1992, 114, 791-792 and references therein.
12. [3a] S. Bräse, A. de Meijere, in: Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim 1998, p. 99-166.
13. [3b] E.-i. Negishi, C. Copéret, S. Ma, S.-Y. Liou, F. Liu, Chem. Rev. 1996, 96, 365-393.
14. [3c] W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7.
15. [3d] A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506;
16. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
17. [3e] R. F. Heck, in: Comprehensive Organic Synthesis, vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, pp. 833-863.
18. [3f] G. D. Daves Jr., A. Hallberg, Chem. Rev. 1989, 89, 1433-1445.
19. [3g] R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985.
20. [4a] K. H. Ang, S. Bräse, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt, A. de Meijere, Tetrahedron 1996, 52, 11503-11528.
21. [4b] F. E. Meyer, K. H. Ang, A. G. Steinig, A. de Meijere, Synlett 1994, 191-193.
22. [5a] T. C. McMorris, M. J. Kelner, R. K. Chadha, J. S. Siegel, S. Moon, M. M. Moya, Tetrahedron 1989, 45, 5433-5440.
23. [5b] M. Anchel, A. Hervey, W. Robbins, J. Proc. Nat. Acad. Sci. U. S. A. 1952, 38, 927.
24. [5c] M. Anchel, A. Hervey, W. Robbins, J. Proc. Nat. Acad. Sci. U. S. A. 1950, 36, 300.
25. [6a] M. Ojika, K. Wakamatsu, H. Niwa, K. Yamda, Tetrahedron 1987, 43, 5261-5274.
26. [6b] S. Ohba, Y. Saito, I. Hirono, H. Niwa, M. Ojika, K. Wakamatsu, K. Yamda, Acta Crystallogr., Sect. C 1984, 40, 1877-1879.
27. [6c] H. Niwa, M. Ojika, K. Wakamatsu, K. Yamda, S. Ohba, Y. Saito, I. Hirono, K. Matsushita, Tetrahedron Lett. 1983, 24, 5371-5372.
28. [7a] D. C. Aldridge, W. B. Turner, J. Chem. Soc. C 1969, 923-928.
29. [7b] D. C. Aldridge, J. J. Armstrong, R. N. Speake, W. B. Turner, J. Chem. Soc., Sect. C 1967, 1667-1676.
30. [8a] S. Lemaire-Audoire, M. Savignac, C. Dupuis, J.-P. Genêt, Tetrahedron Lett. 1996, 37, 2003-2006.
31. [8b] L. Shi, C. K. Narula, K. T. Mak, L. Kao, Y. Xu, R. F. Heck, J. Org. Chem. 1983, 48, 3894-3900.
32. R. Grigg, P. Stevenson, T. Worakun, Tetrahedron 1988, 44, 2033-2048.
33. [10a] T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374.
34. [10b] J. Petránek, M. Vecera, Collect. Czech. Chem. Commun. 1959, 24, 2191-2196.
35. Triphenylphosphane could also be used as a ligand; however, with some combinations of bromodienes 2 and dienophiles 5, separation of the Heck-Diels-Alder products from triphenylphosphane oxide was difficult. Such problems were not encountered with ligands like dppe and 2,9-dimethyl-1,10-phenanthroline.
36. D. Spitzner, H. Swoboda, Tetrahedron Lett. 1986, 27, 1281-1284.
37. [13a] For the synthesis of this highly reactive Michael acceptor and dienophile, see: T. Liese, F. Seyed-Mahdavi, A. de Meijere, Org. Synth. 1990, 69, 148-153.
38. Reviews: [13b] A. de Meijere, L. Wessjohann, Synlett 1990, 20-32.
39. [13c] A. de Meijere, S. I. Kozhushkov, L. P. Hadjiarapoglou, Top. Curr. Chem. 1999, 207, 149-227.
40. J. H. Clark, J. M. Miller, Tetrahedron Lett. 1977, 599-602.
41. [15a] S. D. Larsen, P. A. Grieco, J. Am. Chem. Soc. 1985, 107, 1768-1769.
42. [15b] H. Waldmann, Liebigs Ann. Chem. 1989, 231-238.
43. Y. Hammouda, M. S. Amer, J. Pharm. Sci. 1966, 55, 1452-1454.
44. E. M. Dickinson, G. Jones, Tetrahedron 1969, 25, 1523-1529.
45. M. G. N. Russell, R. Baker, D. C. Billington, A. K. Knight, D. N. Middlemiss, A. J. Noble, J. Med. Chem. 1992, 35, 2025-2033.
46. D. S. Solé, Y. Cancho, A. Llebaria, J. M. Moretó, A. Delgado, J. Org. Chem. 1996, 61, 5895-5904.
47. C. F. Hiskey, H. L. Slates, N. L. Wendler, J. Org. Chem. 1956, 21, 429-433.