Tandem coupling of allyl electrophiles, alkynes, and Me3Al or Me2Zn in the presence of a nickel catalyst

Organometallics

Volumn 17, Issue 19, 1998, Pages 4316-4318

  Ikeda, Shin Ichi ^a   Miyashita, Hitoshi ^a   Sato, Yoshiro ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000285989     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980277w     Document Type: Article

References (20)

1. Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975. Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015. Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. Cui, D.-M.; Yamamoto, H.; Ikeda, S.; Hatano, K.; Sato, Y. J. Org. Chem. 1998, 63, 2782.
2. Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975. Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015. Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. Cui, D.-M.; Yamamoto, H.; Ikeda, S.; Hatano, K.; Sato, Y. J. Org. Chem. 1998, 63, 2782.
3. Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975. Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015. Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. Cui, D.-M.; Yamamoto, H.; Ikeda, S.; Hatano, K.; Sato, Y. J. Org. Chem. 1998, 63, 2782.
4. Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975. Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015. Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. Cui, D.-M.; Yamamoto, H.; Ikeda, S.; Hatano, K.; Sato, Y. J. Org. Chem. 1998, 63, 2782.
5. (a) Ikeda, S.; Cui, D.-M.; Sato, Y. J. Org. Chem. 1994, 59, 6877.
6. (b) Cui, D.-M.; Tsuzuki, T.; Miyake, K.; Ikeda, S.; Sato, Y. Tetrahedron 1998, 54, 1063.
7. Billington, D. C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 423.
8. Chiusoli, G. P. Acc. Chem. Res. 1973, 6, 422. Casser, L.; Chiusoli, G. P.; Guerrieri, F. Synthesis 1973, 509. Llebaria, A.; Moreto. J. Organomet. Chem. 1993, 452, 1.
9. Chiusoli, G. P. Acc. Chem. Res. 1973, 6, 422. Casser, L.; Chiusoli, G. P.; Guerrieri, F. Synthesis 1973, 509. Llebaria, A.; Moreto. J. Organomet. Chem. 1993, 452, 1.
10. Chiusoli, G. P. Acc. Chem. Res. 1973, 6, 422. Casser, L.; Chiusoli, G. P.; Guerrieri, F. Synthesis 1973, 509. Llebaria, A.; Moreto. J. Organomet. Chem. 1993, 452, 1.
11. 3-carbon centers: Sekiya, K.; Nakamura, E. Tetrahedron Lett. 1988, 29, 5155.
12. 2-carbon centers: Tamao, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 467.
13. For the coupling between allylic-carbon and sp-carbon centers: Cui, D.-M.; Hashimoto, N.; Ikeda, S.; Sato, Y. J. Org. Chem. 1995, 60, 5752 and references therein.
14. Scott, W. J.; Crisp, G. T.; Stille, J. K.; J. Am. Chem. Soc. 1984, 106, 4630. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Valle, L. D.; Stelle, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
15. Scott, W. J.; Crisp, G. T.; Stille, J. K.; J. Am. Chem. Soc. 1984, 106, 4630. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Valle, L. D.; Stelle, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
16. Scott, W. J.; Crisp, G. T.; Stille, J. K.; J. Am. Chem. Soc. 1984, 106, 4630. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Valle, L. D.; Stelle, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
17. Scott, W. J.; Crisp, G. T.; Stille, J. K.; J. Am. Chem. Soc. 1984, 106, 4630. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Valle, L. D.; Stelle, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
18. (a) Oppolzer's group developed the cyclization of 9, the so-called "metallo-ene" reaction, using a nickel or palladium catalyst; see: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941. Recently, a palladium-catalyzed reaction of 9 with organometallics was also reported; see: (b) Oppolzer, W.; Ruiz-Montes, J. Helv. Chim. Acta 1993, 76, 1266.
19. (a) Oppolzer's group developed the cyclization of 9, the so-called "metallo-ene" reaction, using a nickel or palladium catalyst; see: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941. Recently, a palladium-catalyzed reaction of 9 with organometallics was also reported; see: (b) Oppolzer, W.; Ruiz-Montes, J. Helv. Chim. Acta 1993, 76, 1266.
20. (a) Oppolzer's group developed the cyclization of 9, the so-called "metallo-ene" reaction, using a nickel or palladium catalyst; see: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941. Recently, a palladium-catalyzed reaction of 9 with organometallics was also reported; see: (b) Oppolzer, W.; Ruiz-Montes, J. Helv. Chim. Acta 1993, 76, 1266.