Stable, storable, and reusable asymmetric catalyst: A novel La-linked- BINOL complex for the catalytic asymmetric Michael reaction [10]

Journal of the American Chemical Society

Volumn 122, Issue 27, 2000, Pages 6506-6507

  Kim, Yun Sik ^a   Matsunaga, Shigeki ^a   Das, Jagattaran ^a   Sekine, Akihiro ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALUMINUM; GALLIUM; LITHIUM; METAL COMPLEX; POLYMER;

CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; ENANTIOMER; LETTER; MOISTURE; SOLUBILITY; TEMPERATURE;

EID: 0001392528     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001036u     Document Type: Letter

References (28)

1. For a recent review, see: Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; 1999; Chapter 38.
2. For examples of recycling of the polymer-supported asymmetric catalysts itself, see: (a) Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051. (b) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918. (d) Heckel, A.; Seebach, D. Angew. Chem., Int. Ed. 2000, 39, 163. (e) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
3. For examples of recycling of the polymer-supported asymmetric catalysts itself, see: (a) Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051. (b) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918. (d) Heckel, A.; Seebach, D. Angew. Chem., Int. Ed. 2000, 39, 163. (e) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
4. For examples of recycling of the polymer-supported asymmetric catalysts itself, see: (a) Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051. (b) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918. (d) Heckel, A.; Seebach, D. Angew. Chem., Int. Ed. 2000, 39, 163. (e) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
5. For examples of recycling of the polymer-supported asymmetric catalysts itself, see: (a) Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051. (b) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918. (d) Heckel, A.; Seebach, D. Angew. Chem., Int. Ed. 2000, 39, 163. (e) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
6. For examples of recycling of the polymer-supported asymmetric catalysts itself, see: (a) Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051. (b) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918. (d) Heckel, A.; Seebach, D. Angew. Chem., Int. Ed. 2000, 39, 163. (e) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
7. For a example of recycling of the polymer-supported metal and the chiral ligand independently, see: Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229.
8. (a) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
9. (b) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
10. For a recent review, see: Lewis Acid Reagents. A Practical Approach; Yamamoto, H., Ed.; Oxford University Press: New York; 1999.
11. Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252.
12. The X-ray data of LiCl free Ga-Li-linked-BINOL complex showed that there was no coordination between oxygen in the linker and gallium. See ref 6.
13. (a) Magnus, P.; Sear, N. L.; Kim, C. S.; Vicker, N. J. Org. Chem. 1992, 57, 70.
14. (b) Shimizu, S.; Ohori, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 7547.
15. Ohori, K.; Shimizu, S.; Ohshima, T.; Shibasaki, M. Chirality, in press.
16. For a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236.
17. For recent reviews, see: (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; 1999; Chapter 31. (b) Tye, H. J. Chem. Soc., Perkin Trans. I 2000, 275.
18. For recent reviews, see: (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; 1999; Chapter 31. (b) Tye, H. J. Chem. Soc., Perkin Trans. I 2000, 275.
19. For a representative example of the catalytic asymmetric Michael reactions of enones with malonates, see: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520.
20. For representative examples of other catalytic asymmetric Michael reactions, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994. (e) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215 and references therein.
21. For representative examples of other catalytic asymmetric Michael reactions, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994. (e) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215 and references therein.
22. For representative examples of other catalytic asymmetric Michael reactions, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994. (e) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215 and references therein.
23. For representative examples of other catalytic asymmetric Michael reactions, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994. (e) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215 and references therein.
24. For representative examples of other catalytic asymmetric Michael reactions, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994. (e) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215 and references therein.
25. 3 can be purchased from Kojundo Chemical Laboratory Co., Ltd., 5-1-28, Chiyoda, Sakado-shi, Saitama 350-0214, Japan (Fax: +(81)-492-84-1351).
26. Computational optimization of a model compound (La-linked-biphenol complex) using molecular mechanics calculation followed by ab initio calculation indicated that the distance between lanthanum and oxygen in the linker should be 2.62-2.69 Å, which is nearly equal to that between lanthanum and phenolic oxygen (2.58-2.65 Å). It seems reasonable to consider that the oxygen atom in the linker would also function as coordinative moiety and thus linked-BINOL would function as pentadentate ligand toward La, thus making the La-linked-BINOL complex 4 unusually stable. See Supporting Information for details and references of the calculation.
27. The absolute configurations of 3, 12-17, and 25 have already been determined. See Supporting Information. The absolute configurations of 18, 19, 21, and 22 were tentatively determined on the basis of the previous results. See ref 9.
28. The recovered powdered complex 4 contained ∼10-15% of 3.