Immobilization and reuse of Pd complexes in ionic liquid: Efficient catalytic asymmetric fluorination and Michael reactions with β-ketoesters

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3225-3228

  Hamashima, Yoshitaka ^a,b   Takano, Hisashi ^a,b   Hotta, Daido ^a,b   Sodeoka, Mikiko ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; ORGANIC SOLVENT; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; FLUORINATION; LIQUID; METAL RECOVERY; MICHAEL ADDITION;

EID: 0141632776     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035053a     Document Type: Article

References (39)

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9. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
10. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
11. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
12. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
13. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
14. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
15. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
16. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
17. Recent selected examples: Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219-2222. (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893-895. (d) Zerth, H. M.; Leonard, N, M.; Mohan, R. S. Org. Lett. 2003, 5, 55-57. (e) Boxwell, C. V.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334-9335. (f) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229. (g) Yao, Q. Org. Lett. 2002, 4, 2197-2199. (h) Mehnert, C. P.; Dispenziere, N. C.; Cook, R. A. Chem. Commun. 2002, 1610-1611. (i) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2002 1249-1250. See also ref 4.
18. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
19. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
20. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
21. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
22. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
23. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
24. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
25. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
26. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
27. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
28. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
29. Hydrogenation: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700. (b) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J. Tetrahedron: Asymmetry 1997, 2, 177-179. (c) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254-1255. (d) Guernik, S.; Wolfson, A.; Herskowitz, M.; Greenspoon, N.; Geresh, S. Chem. Commun. 2001, 2314-2315. Epoxidation: (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838. Dihydroxylation: (f) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036-3037. (g) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038-3039. Aldol reaction: (h) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741-8743. (i) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510-2511. Cyclopropanation: (j) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891-1894. Epoxide opening reaction: (k) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743-1744. (l) Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chem. Commun. 2003, 1100-1101.
30. Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
31. Hamashima, Y.; Yagi, K.; Takano, H.; Tamás, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530-14531.
32. Unpublished results: we recently found that the Michael reaction proceeded in water without any organic solvent. In the case of tert-butyl 2-oxo-1-cyclopentanecarboxylate 3c, the reaction with MVK was completed after 24 h at 4°C to give the product in 92% yield and 88% ee.
33. These ionic liquids were purchased from ACROS and used directly without further purification.
34. Recently, an enantioselective fluorination in IL was reported using a stoichiometric amount of fluorinating reagents derived from cinchona alkaloid: Baudequin, C.; Plaquevent, J.-C.; Audouard, C.; Cahard, D. Green Chemistry, 2002, 4, 584-586.
35. Although the reason is not clear, reaction rate apparently depends on the nature of the substrates.
36. Representative Procedure for Fluorination. To a stirred solution of Pd-cat. 1a (15.4 mg, 7.4 μmol) in IL 9 (0.3 mL) were added 3a (70 μL, 0.3 mmol) and NFSI (142 mg, 0.46 mmol) at room temperature. After the completion of the reaction (TLC), ether (2 mL 5 10) was added for extraction. Ether was withdrawn via a syringe, and the combined ether layers were concentrated. The resulting residue was purified by short column chromatography (hexane/ether = 10/1) to give the pure product. The absolute configuration of the product was determined to be R on the basis of the HPLC analysis The separated ionic liquid layer was directly reused as a catalyst solution in the next reaction.
37. 2. See: Dell'Anna, M. M.; Gallo, V.; Mastrorilli, P.; Nobile, C. F.; Romanazzi, G.; Suranna, G. P. Chem. Comm. 2002, 434-435.
38. Representative Procedure for Michael Reaction. To a stirred ionic liquid (IL 8, 0.2 mL) solution of Pd catalyst 2b (8.4 mg, 0.0075 mmol) recovered from fluorination were added 3c (55 μL, 0.3 mmol) and MVK (50 μL, 0.6 mmol) at 0°C. After the time shown in Table 3, the product was extracted by adding ether (2 mL x 8). From the combined ether layers, 6c was isolated by flash column chromatography (hexane/ethyl acetate = 5/1) as a colorless oil. The absolute configuration of the product was determined to be R on the basis of the HPLC analysis.
39. Although the exact role of benzenesulfonimde is unclear so far, the following preliminary results showed its positive role in this reaction. Thus, the control experiment was carried out with the freshly prepared 2b in the presence of benzenesulfonimide (2 equiv to Pd) as an additive, and the comparable results were obtained after 5 cycles (96%, 86% ee, after 10 h at 0°C). The usage of NFSI (2 equiv to Pd) instead of benzenesulfonimide gave almost the same results after 5 cycles. Therefore, the catalyst recycle in the Michael reaction may be attributed to benzenesulfonimide. The details of these experiments will be reported in due course.