Pauson-Khand reaction induced by molecular sieves

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1187-1188

  Pérez Serrano, Leticia ^a   Casarrubios, Luis ^a   Domínguez, Gema ^a   Pérez Castells, Javier ^a  

^a UNIVERSIDAD SAN PABLO CEU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040830739     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990856c     Document Type: Article

References (22)

1. Recent reviews on the Pauson-Khand reaction: (a) Geis, O.; Schmalz, H.-G. Angew. Chem. Int. Ed. Engl. 1998, 37, 911-914.
2. (b) Ingate, S. T.; Marco-Contelles, J. Org. Proc. Prep. Int. 1998, 123-142.
3. (c) Shore, N. E. In Comprehensive Organometallic Chemistry II, Hegedus, L. S., Ed.; Pergamon Press: 1995; Vol. 12, pp 703-739.
4. For some recent examples of natural product syntheses, see: (a) Kowalczyk, B. A.; Shmith, T. C.; Dauben, W. G. J. Org. Chem. 1998, 63, 1379-1389.
5. (b) Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 3346-3351.
6. (c) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 4353-4363.
7. (a) Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S. E.; Sunghee, H. Synlett 1991, 204-206.
8. (b) Shambayati, S.; Crowe, W. E.; Schreiber, S. Tetrahedron Lett. 1990, 31, 5289-5292.
9. Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220-223.
10. (a) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801-2803.
11. (b) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384-1386.
12. Smit, W. A.; Gybin, A. S.; Shaskov, A. S.; Strychkov, Y. T.; Kyzmina, L. G.; Mikaelian, G. S.; Caple, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241-1244.
13. Castro, J.; Moyano, A.; Pericás, M. A.; Riera, A.; Greene, A. E. Tetrahedron: Asymmetry 1994, 5, 307-310.
14. Hoye, T.; Suriano, J. A. J. Org. Chem. 1993, 58, 1659-1660.
15. Blanco-Urgoiti, J.; Casarrubios, L.; Pérez-Castells, J. Tetrahedron Lett. 1999, 40, 2817-2820.
16. (a) Antonioletti, R.; Bonadies, F.; Locati, L.; Scettri, A. Tetrahedron Lett. 1992, 33, 3205-3206.
17. (b) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922-1925.
18. Koga, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1994, 35, 1227-1230.
19. (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345.
20. (b) Dessau, R. M. J. Chem. Soc., Chem. Commun. 1986, 1167-1168.
21. Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021-4024.
22. 3NO (9.0 mmol) in toluene at 0°C was added dropwise. After 18 h of stirring and filtration, the solvent was evaporated under vacuum and the crude product purified by flash chromatography (hexanes/EtOAc mixtures).