The Polymer Effect on Catalysts. Aldimine-Selective Reactions in the Coexistence of Aldehydes Using a Polymer-Supported Scandium Catalyst

Synlett

Volumn 1997, Issue 6, 1997, Pages 653-654

  Kobayashi, Shu ^a   Nagayama, Satoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002370337     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3263     Document Type: Article

References (17)

1. (a) Solid Supports and Catalysts in Organic Synthesis Smith, K. Ed.; Ellis Hornood: Chichester, 1992.
2. (b) Synthesis and Separations Using Functional Polymers Sherrington, D. C.; Hodge, P. Eds.: John Wiley & Sons Inc.: New York, 1988.
3. (c) Blazer, H. U.; Pugin, B. In Chiral Reactions in Heterogeneous Catalysis, Jannes, G.; Dubois, J. Eds., Plenum Press: New York, 1995.
4. For example, (a) Bailar, J. C., Jr. Catal. Rev.-Sci. Eng. 1974, 10, 17. (b) Pittman, C. U.; Jacobson, S.E. J. Mol. Catal. 1978, 3, 293. (c) Dawans, F.; Morel, D. ibid. 1978, 3, 403. (d) Carlini, C.; Braca, G.; Ciardelli, F.; Sbrana, G. ibid. 1977, 2, 379. (e) Capka, M.; Svoboda, P.; Cerny, M.; Hetflejs, J. Tetrahedron Lett. 1971, 3787. (f) Brown, J. M.; Morinari, H. Tetrahedron Lett. 1979, 2933. (g) Pinna, F.; Bonivento, M.; Strukul, G.; Graziani, M.; Cernia, E.; Palladino, N. J. Mol. Catal. 1976, 1, 309.
5. For example, (a) Bailar, J. C., Jr. Catal. Rev.-Sci. Eng. 1974, 10, 17. (b) Pittman, C. U.; Jacobson, S.E. J. Mol. Catal. 1978, 3, 293. (c) Dawans, F.; Morel, D. ibid. 1978, 3, 403. (d) Carlini, C.; Braca, G.; Ciardelli, F.; Sbrana, G. ibid. 1977, 2, 379. (e) Capka, M.; Svoboda, P.; Cerny, M.; Hetflejs, J. Tetrahedron Lett. 1971, 3787. (f) Brown, J. M.; Morinari, H. Tetrahedron Lett. 1979, 2933. (g) Pinna, F.; Bonivento, M.; Strukul, G.; Graziani, M.; Cernia, E.; Palladino, N. J. Mol. Catal. 1976, 1, 309.
6. For example, (a) Bailar, J. C., Jr. Catal. Rev.-Sci. Eng. 1974, 10, 17. (b) Pittman, C. U.; Jacobson, S.E. J. Mol. Catal. 1978, 3, 293. (c) Dawans, F.; Morel, D. ibid. 1978, 3, 403. (d) Carlini, C.; Braca, G.; Ciardelli, F.; Sbrana, G. ibid. 1977, 2, 379. (e) Capka, M.; Svoboda, P.; Cerny, M.; Hetflejs, J. Tetrahedron Lett. 1971, 3787. (f) Brown, J. M.; Morinari, H. Tetrahedron Lett. 1979, 2933. (g) Pinna, F.; Bonivento, M.; Strukul, G.; Graziani, M.; Cernia, E.; Palladino, N. J. Mol. Catal. 1976, 1, 309.
7. For example, (a) Bailar, J. C., Jr. Catal. Rev.-Sci. Eng. 1974, 10, 17. (b) Pittman, C. U.; Jacobson, S.E. J. Mol. Catal. 1978, 3, 293. (c) Dawans, F.; Morel, D. ibid. 1978, 3, 403. (d) Carlini, C.; Braca, G.; Ciardelli, F.; Sbrana, G. ibid. 1977, 2, 379. (e) Capka, M.; Svoboda, P.; Cerny, M.; Hetflejs, J. Tetrahedron Lett. 1971, 3787. (f) Brown, J. M.; Morinari, H. Tetrahedron Lett. 1979, 2933. (g) Pinna, F.; Bonivento, M.; Strukul, G.; Graziani, M.; Cernia, E.; Palladino, N. J. Mol. Catal. 1976, 1, 309.
8. For example, (a) Bailar, J. C., Jr. Catal. Rev.-Sci. Eng. 1974, 10, 17. (b) Pittman, C. U.; Jacobson, S.E. J. Mol. Catal. 1978, 3, 293. (c) Dawans, F.; Morel, D. ibid. 1978, 3, 403. (d) Carlini, C.; Braca, G.; Ciardelli, F.; Sbrana, G. ibid. 1977, 2, 379. (e) Capka, M.; Svoboda, P.; Cerny, M.; Hetflejs, J. Tetrahedron Lett. 1971, 3787. (f) Brown, J. M.; Morinari, H. Tetrahedron Lett. 1979, 2933. (g) Pinna, F.; Bonivento, M.; Strukul, G.; Graziani, M.; Cernia, E.; Palladino, N. J. Mol. Catal. 1976, 1, 309.
9. For example, (a) Bailar, J. C., Jr. Catal. Rev.-Sci. Eng. 1974, 10, 17. (b) Pittman, C. U.; Jacobson, S.E. J. Mol. Catal. 1978, 3, 293. (c) Dawans, F.; Morel, D. ibid. 1978, 3, 403. (d) Carlini, C.; Braca, G.; Ciardelli, F.; Sbrana, G. ibid. 1977, 2, 379. (e) Capka, M.; Svoboda, P.; Cerny, M.; Hetflejs, J. Tetrahedron Lett. 1971, 3787. (f) Brown, J. M.; Morinari, H. Tetrahedron Lett. 1979, 2933. (g) Pinna, F.; Bonivento, M.; Strukul, G.; Graziani, M.; Cernia, E.; Palladino, N. J. Mol. Catal. 1976, 1, 309.
10. For example, (a) Bailar, J. C., Jr. Catal. Rev.-Sci. Eng. 1974, 10, 17. (b) Pittman, C. U.; Jacobson, S.E. J. Mol. Catal. 1978, 3, 293. (c) Dawans, F.; Morel, D. ibid. 1978, 3, 403. (d) Carlini, C.; Braca, G.; Ciardelli, F.; Sbrana, G. ibid. 1977, 2, 379. (e) Capka, M.; Svoboda, P.; Cerny, M.; Hetflejs, J. Tetrahedron Lett. 1971, 3787. (f) Brown, J. M.; Morinari, H. Tetrahedron Lett. 1979, 2933. (g) Pinna, F.; Bonivento, M.; Strukul, G.; Graziani, M.; Cernia, E.; Palladino, N. J. Mol. Catal. 1976, 1, 309.
11. For example, Yamaguchi, M. In Comprehensive Organic Synthesis Trost, B. M. Ed.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1.11.
12. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
13. 3 is an excellent catalyst in the aldol reactions of aldehydes with silyl enolates and in the iminoaldol reactions of aldimines with silyl enolates. (a) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472. (b) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (c) Kobayashi, S. Synlett 1994, 689.
14. 3 is an excellent catalyst in the aldol reactions of aldehydes with silyl enolates and in the iminoaldol reactions of aldimines with silyl enolates. (a) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472. (b) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (c) Kobayashi, S. Synlett 1994, 689.
15. 3 is an excellent catalyst in the aldol reactions of aldehydes with silyl enolates and in the iminoaldol reactions of aldimines with silyl enolates. (a) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472. (b) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (c) Kobayashi, S. Synlett 1994, 689.
16. PA-Sc-TAD = Polyallylscandium trifylamide ditriflate. As for the reactions using PA-Sc-TAD, see (a) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (b) Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron Lett. 1996, 37, 9221.
17. PA-Sc-TAD = Polyallylscandium trifylamide ditriflate. As for the reactions using PA-Sc-TAD, see (a) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (b) Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron Lett. 1996, 37, 9221.