Palladium-catalyzed intramolecular coupling of vinyl halides and ketone enolates. Synthesis of bridged azabicyclic compounds

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2225-2227

  Solé, Daniel ^a   Peidró, Emma ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000212607     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005973i     Document Type: Article

References (32)

1. (a) Bonjoch, J.; Solé, D.; García-Rubio, S.; Bosch, J. J. Am. Chem. Soc. 1997, 119, 7230-7240.
2. (b) Quirante, J.; Escolano, C.; Merino, A.; Bonjoch, J. J. Org. Chem. 1998, 63, 968-976.
3. (c) Sole, D.; Bonjoch, J.; García-Rubio, S.; Peidró, E.; Bosch, J. Chem. Eur. J. 2000, 6, 655-665.
4. (a) Isolation: Tits, M.; Tavernier, D.; Angenot, L. Phytochemistry 1980, 19, 1531-1534.
5. (b) Synthetic studies: Teuber, H.-J.; Tsaklakidis, C.; Bats, J. W. Liebigs Ann. Chem. 1992, 461-466.
6. (a) Isolation: Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanihi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37-44.
7. (b) Total synthesis: Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778-7786.
8. For our studies in this field, see: Bonjoch, J.; Diaba, F.; Puigbó, G.; Sole, D.; Segarra, V.; Santamaría, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Bioorg. Med. Chem. 1999, 7, 2891-2897.
9. (a) Isolation: Kong, F.; Andersen, R. J.; Allen, T. M. J. Am. Chem. Soc 1994, 116, 6007-6008.
10. (b) Synthetic studies: Matzanke, N.; Gregg, R. J.; Weinreb, S. M. J. Org. Chem. 1997, 62, 1920-1921.
11. For the Pd-catalyzed intramolecular coupling of aryl halides and enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581-7582.
12. (b) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546-6553.
13. (c) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355-2358.
14. For the Pd-catalyzed intermolecular coupling of aryl halides and enolates, see: (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370 and references therein.
15. (a) Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454-3455.
16. (b) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11-13.
17. For the elaboration of 3-alkylidene piperidine rings by Heck reactions in the synthesis of alkaloids, see: (a) Rawal, V. H.; Michoud, C.; Monestel, R. F.J. Am. Chem. Soc. 1993, 115, 3030-3031. Rawal, V. H.; Iwasa, S. J. Org. Chem. 1994, 59, 2685-2686.
18. For the elaboration of 3-alkylidene piperidine rings by Heck reactions in the synthesis of alkaloids, see: (a) Rawal, V. H.; Michoud, C.; Monestel, R. F.J. Am. Chem. Soc. 1993, 115, 3030-3031. Rawal, V. H.; Iwasa, S. J. Org. Chem. 1994, 59, 2685-2686.
19. (b) Birman, V. B.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 7219-7222. Birman, V. B.; Rawal, V. H. J. Org. Chem. 1998, 63, 9146-9147.
20. (b) Birman, V. B.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 7219-7222. Birman, V. B.; Rawal, V. H. J. Org. Chem. 1998, 63, 9146-9147.
21. (c) See ref 1c.
22. Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391-1402.
23. For other recent synthetic methods to build up this azabicyclic system, see: (a) Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429.
24. (b) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281.
25. (c) Quirante, J.; Escolano, C.; Diaba, F.; Bonjoch, J. J. Chem. Soc., Perkin Trans. 1 1999, 1157-1162.
26. 7a
27. 6b,d has also been tried as a base for this process. Using the reaction conditions of entry 1 (Table 1) and the aforementioned base, there was no significant change in the yield of compound 1.
28. 3SnF, see: Kuwajima, I.; Urabe, H. J. Am. Chem. Soc. 1982, 104, 6831-6833.
29. 3-SnOMe, see: Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull. Chem. Soc. Jpn. 1984, 37, 242-246.
30. Quirante, J.; Escolano, C.; Bonjoch, J. Synlett 1997, 179-180.
31. 7a
32. For the easy air oxidation of 3-acylpyrrolines to 3-acylpyrroles, see: Chou, S.-S. P.; Yuan, T.-M. Synthesis 1991, 171-172.