Nickel-catalyzed three-component connection reaction of dimethylzinc, 1,ω-ene-diene, and acetone: Synthesis of 1,2-disubstituted cycloalkanes

Synthesis

Volumn , Issue 18, 2004, Pages 3089-3091

  Kimura, Masanari ^a   Kojima, Keisuke ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Catalysis; Cyclization; Diene; Nickel; Organozinc

Indexed keywords

CATALYSIS; NICKEL; OLEFINS; ORGANOMETALLICS;

CYCLIZATION; CYCLOALKANES; STEREOSELECTIVITY;

ACETONE;

1,3,8 NONATRIENE; 1,3,9 DECATRIENE; ACETONE; ALKADIENE; DIMETHYLZINC; NICKEL; TRIENTINE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 11144341887     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834908     Document Type: Article

References (19)

1. (a) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem. Int. Ed. 2002, 41, 2784.
2. (b) Kimura, M.; Ezoe, A.; Mori, M.; Tamaru, Y. J. Am. Chem. Soc. 2004, in press.
3. Protocols for this type of Ni-catalyzed addition of dienes to aldehydes: (a) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033.
4. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 397.
5. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624.
6. (d) Shibata, K.; Kimura, M.; Shimizu, M.; Tamaru, Y. Org. Lett. 2001, 3, 2181.
7. (e) Kimura, M.; Ezoe, A.; Tanaka, S.; Tamaru, Y. Angew. Chem. Int. Ed. 2001, 40, 3600.
8. (f) Sato, Y.; Sawaki, R.; Saito, N.; Mori, M. J. Org. Chem. 2002, 67, 656.
9. (g) Kimura, M.; Miyachi, A.; Kojima, K.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2004, in press.
10. Protocols of this type Ni-catalyzed oxidative cyclization of alkynes and alkenes: (a) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775.
11. (b) Mahandru, G. M.; Skauge, A. R. L.; Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 13481.
12. (c) Review: Montgomery, J. Angew. Chem. Int. Ed. 2004, 43, 3890.
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14. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994, 776.
15. To the best of our knowledge, this is the first example of transition-metal catalyzed cyclization of 1,3,8-nonatrienes and 1,3,9-decatrienes (3) except the transition-metal catalyzed Diels-Alder reaction: O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
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17. (a) Kimura, M.; Matsuo, S.; Shibata, K.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 3386.
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19. (c) Shibata, K.; Kimura, M.; Kojima, K.; Tanaka, S.; Tamaru, Y. J. Organomet. Chem. 2001, 624, 348.