Palladium-catalyzed [2+2] cycloaddition of allylic acetates and norbornene

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4181-4184

  Tsukada, Naofumi ^a   Sato, Tetsuo ^a   Inoue, Yoshio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Allylation; Catalysis; Cycloaddition

Indexed keywords

ACETIC ACID; ALKADIENE; ALLYL COMPOUND; NORBORNENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY;

EID: 0034729521     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00600-6     Document Type: Article

References (24)

1. (a) Godleski, S. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 3.3.
2. (b) Tsuji, J.; In Palladium Reagents and Catalysts, Innovations in Organic Synthesis; Wiley: London, 1995; p. 290.
3. (c) Baker, R. Chem. Rev. 1973, 73, 487-530.
4. For allylation of carbonyl compounds, see also: (d) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647.
5. (e) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114.
6. For reviews, see: (a) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 8.3.
7. (b) Oppolzer, W. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, Chapter 1.2.
8. (a) Oppolzer, W.; Ruiz-Montes, J. Helv. Chim. Acta. 1993, 76, 1266-1274.
9. (b) Ihle, N. C.; Heathcock, C. H. J. Org. Chem. 1993, 58, 560-563.
10. (c) Hiroi, K.; Hirasawa, K. Chem. Pharm. Bull. 1994, 42, 786-791.
11. (d) Doi, T.; Yanagisawa, A.; Nakanishi, S.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1996, 61, 2602-2603.
12. (e) Gómez-Bengoa, E.; Cuerva, J. M.; Echavarren, A. M.; Martorell, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 767-769.
13. (a) Amari, E.; Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1985, 285, 383-388.
14. (b) Fugami, K.; Enokido, T.; Kawata, K.; Kameyama, M.; Kosugi, M. Main Group Met. Chem. 1999, 22, 511-514.
15. (a) Zocchi, M.; Tieghi, G.; Albinati, A. J. Organomet. Chem. 1971, 33, C47-C48.
16. (b) Zocchi, M.; Tieghi, G.; Albinati, A. J. Chem. Soc., Dalton Trans. 1973, 883-885.
17. (c) Zocchi, M.; Tieghi, G. J. Chem. Soc., Dalton Trans. 1979, 944-947.
18. (d) Larock, R. C.; Takagi, K.; Burkhart, J. P.; Hershberger, S. S. Tetrahedron Lett. 1986, 3759-3762.
19. (e) Direnzo, G. M.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 6225-6234.
20. See also: (e) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007-8008.
21. Catellani, M.; Chiusoli, G. P.; Dradi, E.; Salerno, G. J. Organomet. Chem. 1979, 177, C29-C31.
22. Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 655-657.
23. (a) Catellani, M.; Chiusoli, G. P.; Giroldini, W.; Salerno, G. J. Organomet. Chem. 1980, 199, C21-C23.
24. (b) Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1982, 233, C21-C24.