Simple Strategy for the Immobilization of Dirhodium Tetraprolinate Catalysts Using a Pyridine-Linked Solid Support

Journal of the American Chemical Society

Volumn 126, Issue 13, 2004, Pages 4271-4280

  Davies, Huw M L ^a   Walji, Abbas M ^a   Nagashima, Tadamichi ^a,b  

^a UNIVERSITY AT BUFFALO   (United States)

^b Fluorous Technologies   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST IMMOBILIZATION; CYCLOPROPANATION;

CATALYSTS; CROSSLINKING; POLYSTYRENES; STEREOCHEMISTRY;

ORGANOMETALLICS;

AZO COMPOUND; DIAZOACETIC ACID ETHYL ESTER; DIRHODIUM TETRACARBOXYLATE; DIRHODIUM TETRAPROLINATE; METHYL PHENYLDIAZOACETATE; POLYMER; POLYSTYRENE; PROLINE DERIVATIVE; PYRIDINE DERIVATIVE; RHODIUM DERIVATIVE; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOPROPANATION; ENANTIOSELECTIVITY; ENCAPSULATION; REACTION ANALYSIS; SOLID STATE;

EID: 1842607371     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0393067     Document Type: Article

References (52)

1. (a) Chiral Catalysts Immobilization and Recycling; De Vos, D. E., Vankelecom I. F. J., Jacobs, P. A., Eds.; Wiley-VCH: Weinheim, Germany, 2000.
2. (b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637.
3. (c) Sherrington, D. C. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 2364.
4. (d) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. In Solid-Phase Organic Synthesis; Burgess, K., Ed.; Wiley-Interscience: New York, 2000; pp 149-194.
5. (e) de Miguel, Y. D.; Bryle, E.; Margue, R. G. J. Chem. Soc., Perkin Trans. I 2001, 3085-3094.
6. Davies, H. M. L.; Antoulinakis, E. G. Org. React. 2001, 57, 1-326.
7. (a) Davies, H. M. L.; Beckwith, R. J. W. Chem. Rev. 2003, 103, 2861.
8. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. In Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998.
9. (a) Bergbreiter, D. E.; Chen, B.; Morvant, M. Tetrahedron Lett. 1991, 32, 2731.
10. (b) Doyle, M. P.; Eismont, M. Y.; Bergbreiter, D. E.; Gray, H. N. J. Org. Chem. 1992, 57, 6103.
11. (c) Burguette, M. I.; Fraile, J. M.; Garcia, J. I.; Garcia-Verdugo, E.; Luis, S. V.; Mayoral, J. A. Org. Lett. 2000, 2, 3905.
12. (d) Burguette, M. I.; Fraile, J. M.; Garcia, J. I.; Garcia-Verdugo, E.; Luis, S. V.; Mayoral, J. A. J. Org. Chem. 2001, 66, 8893.
13. (e) Diaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Perez, P. J. Organometallics 2000, 19, 285.
14. (f) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045.
15. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pitillo, M. J. Org. Chem. 2001, 66, 3160.
16. (h) Doyle, M. P.; Timmons, D. J.; Tumonis, S. J.; Gau, H.; Blossey, C. E. Organometallics 2002, 21, 1747.
17. (i) Cornejo, A.; Fraile, J. M.; Garcia, J. I.; Garcia-Verdugo, E.; Gil, M. J.; Legarreta, G.; Luis, V. S.; Martinez-Merino, V.; Mayoral, J. A. Org. Lett. 2002, 4, 3927.
18. For reviews, see: (j) Rechavi, D.; Lemaire, M. Chem. Rev. 2002, 102, 3467.
19. (k) Bergbreiter, D. E. In Chiral Catalyst Immobilization and Recycling; De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds.; Wiley-VCH: Weinheim, Germany, 2000; p 43.
20. Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Vincent, M. J.; Mayoral, J. A. React. Polym. 2001, 48, 25.
21. (a) Reference 3a.
22. (b) Davies, H. M. L.; Antoulinakis, E. G. J. Organomet. Chem. 2001, 617-618, 47.
23. (c) Davies, H. M. L. J. Mol. Catal 2002, 189, 125.
24. (d) Davies, H. M. L. Eur. J. Org. Chem. 1999, 2459.
25. Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989.
26. Davies, H. M. L.; Walji, A. M. Org. Lett. 2003, 5, 479.
27. Purchased from Argonaut Technologies (www.argotech.com).
28. Dorwald, F. Z. In Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, Germany, 2000.
29. Wang, S.-S. J. Am. Chem. Soc. 1973, 95, 1328.
30. Asymmetric cyclopropanations of aryldiazoacetates are routinely highly diastereoselective. Throughout these studies >92% de was observed and is therefore not reported for each reaction. (a) Davies, H. M. L.; Bruzinski, P. R.; Fall, M. J. Tetrahedron Lett. 1996, 37, 4133.
31. (b) Doyle, M. P.; Zhou, Q.-L.; Charnsangavej, C.; Longoria, M. A.; McKervey, M. A.; Garcia, C. F. Tetrahedron Lett. 1996, 37, 4129.
32. (a) Kobayashi, S.; Endo, M.; Nagayama, S. Org. Lett. 2001, 3, 2649.
33. (b) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229.
34. (c) Nagayama, S.; Endo, M.; Kobayashi, S. J. Org. Chem. 1998, 63, 6094.
35. (d) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
36. Purchased from Aldrich Chemical Co. (www.sigma-aldrich.com).
37. (a) Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40, 6329.
38. (b) Reger, T. S.; Janda, K. D. J. Am. Chem. Soc. 2000, 122, 6929.
39. (c) Garibay, P.; Toy, P. H.; Hoeg-Jensen, T.; Janda, K. D. Synlett 1999, 9, 1438.
40. (d) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 6801.
41. (e) Toy, P. H.; Reger, T. S.; Janda, K. D. Aldrichimica Acta 2000, 33, 87.
42. (f) Toy, P. H.; Reger, T. S.; Garibay, P.; Garno, J. C.; Malikayil, J. A.; Liu, G.; Janda, K. D. J. Comb. Chem. 2001, 3, 117.
43. Davies, H. M. L.; Venkataramani, C. Org. Lett. 2003, 5, 1403.
44. (a) Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 10139.
45. (b) Rebek, J.; Gavina, F. J. Am. Chem. Soc. 1974, 96, 7112.
46. (c) Rebek, J.; Brown, D.; Zimmerman, S. J. Am. Chem. Soc. 1975, 97, 454.
47. (d) Rebek, J., Jr. Tetrahedron 1979, 35, 723.
48. (a) Clapham, B.; Spanka, C.; Janda, K. D. Org. Lett. 2001, 3, 2173.
49. (b) Iso, Y.; Shindo, H.; Hamana, H. Tetrahedron 2000, 56, 5353-5361.
50. (c) Gowravaram, M. R.; Gallop, M. A. Tetrahedron Lett. 1997, 38, 6973.
51. (d) Zaragoza, F.; Petersen, S. V. Tetrahedron 1996, 52, 5000.
52. (e) Cano, M.; Camps, F.; Joglar, J. Tetrahedron Lett. 1998, 39, 9819.