Highly Enantioselective Catalytic Carbon Dioxide Incorporation Reaction: Nickel-Catalyzed Asymmetric Carboxylative Cyclization of Bis-1,3-dienes

Journal of the American Chemical Society

Volumn 126, Issue 19, 2004, Pages 5956-5957

  Takimoto, Masanori ^a   Nakamura, Yoichi ^a   Kimura, Kaoru ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; BIS 1,3 DIENE; CARBON DIOXIDE; LIGAND; METAL; NICKEL; PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CARBOXYLATIVE CYCLIZATION; ASYMMETRIC CATALYSIS; CARBOXYLATION; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 2442421189     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049506y     Document Type: Article

References (20)

1. Reviews: Arakawa, H.; Aresta, M.; Armor, J. N.; Barteau, M. A.; Beckman, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Domen, K.; DuBois, D. L.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. A.; Goodman, W.; Keller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer, L. E. ; Marks, T. J.; Morokuma, K.; Nicholas, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Somorjai, G. A.; Stair, P.; Stults, B. R.; Tumas, W. Chem. Rev. 2001, 101, 953.
2. 2 have recently been reported. (a) Nozaki, K.; Nakano, K.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 11008.
3. (b) Nakano, K.; Nozaki, K.; Hiyama, T. J. Am. Chem. Soc. 2003, 125, 5501.
4. (c) Cheng, M.; Darling, N. A.; Lobkovsky, E. B.; Coates, G. W. Chem. Commun. 2000, 30, 2007.
5. Reviews: (a) Behr, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 661.
6. (b) Braunstein, P.; Matt, D., Nobel, D. Chem. Rev. 1988, 88, 747.
7. (c) Leitner, W. Coord. Chem. Rev. 1996, 153, 257.
8. (d) Yin, X.; Moss, J. R. Coord. Chem. Rev. 1999, 181, 27.
9. (e) Walther, D.; Ruben, M.; Rau, S. Coord. Chem Rev. 1999, 182, 67.
10. 2 under mild conditions. Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am Chem. Soc. 2002, 124, 15188.
11. (a) Takimoto, M.; Mori, M. J. Am. Chem Soc. 2001, 123, 2895.
12. (b) Takimoto, M.; Shimizu, K.; Mori, M. Org. Lett. 2001, 3, 3345.
13. (c) Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2002, 124, 10008.
14. (d) Shimizu, K. Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323.
15. (e) Takimoto, M. Kawamura, M.; Mori, M. Org. Lett. 2003, 5, 2599. For recent examples reported from other laboratories, see ref 6 and references cited in ref 3.
16. Saito, S.; Nakagawa, S.; Koizumi, T.; Hirayama, K.; Yamamoto, Y. J. Org. Chem. 1998, 64, 3975.
17. For reviews on enantioselective reactions using MOP derivatives, see: (a) Hayashi, T. Acc. Chem. Res. 2000, 33, 354.
18. For preparation of MeO-MOP, see: (b) Uozumi, Y.; Kawatsura, M.; Hayashi, T. Org. Synth. 2002, 78, 1.
19. (c) Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945.
20. Nagai, Y.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853. For details, see Supporting Information.