Assessing the suitability of 1,2,3-triazole linkers for covalent immobilization of chiral ligands: Application to enantioselective phenylation of aldehydes

Journal of Organic Chemistry

Volumn 72, Issue 7, 2007, Pages 2460-2468

  Bastero, Amaia ^a   Font, Daniel ^a   Pericàs, Miquel A ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; CHIRALITY; COVALENT BONDS; ENANTIOSELECTIVITY; LIGANDS; RESINS;

AMINO ALCOHOL; CHIRAL LIGANDS; PHENYLATION;

NITROGEN COMPOUNDS;

ALDEHYDE DERIVATIVE; ALKYNYL GROUP; AMINOALCOHOL; AZIDE; CARBON; COPPER; LIGAND; PHENYL GROUP; POLYSTYRENE DERIVATIVE; RESIN; TRIAZOLE DERIVATIVE; ZINC;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COVALENT BOND; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIPOLE; ENANTIOSELECTIVITY; MOLECULAR MODEL; PHENYLATION; REACTION ANALYSIS;

EID: 34047194291     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0624952     Document Type: Article

References (61)

1. Reviews on immobilized catalysts include the following: (a) Immobilized Catalysts: Solid Phases, Immobilization and Applications. In Topics in Current Chemistry; Kirschning, A., Ed.; Springer GmbH: Berlin, 2004; Vol. 242, pp 1-336.
2. (b) In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, D. R., Ed.; VCH Publishers: Weinheim, 2003.
3. For a recent review, see: Jas, G.; Kirschning, A. Chem. Eur. J. 2003, 9, 5708-5723.
4. Jacobs, P. A.; Devos, D. E.; Vankelecom, I. F. J. Chiral Catalyst Immobilization and Recycling; VCH Publishers: Weinheim, 2000.
5. (a) Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970-4982.
6. (b) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
7. (a) Pericàs, M. A.; Castellnou, D.; Rodriguez, I.; Riera, A.; Solà, L. Adv. Synth. Catal. 2003, 345, 1305-1313.
8. (b) Castellnou, D.; Solà, L.; Jimeno, C.; Fraile, J. M.; Mayoral, J. A.; Riera, A.; Pericàs, M. A. J. Org. Chem. 2005, 70, 433-438.
9. (c) Castellnou, D.; Fontes, M.; Jimeno, C.; Font, D.; Solà, L.; Verdaguer, X.; Pericàs, M. A. Tetrahedron 2005, 61, 12111-12120.
10. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
11. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176.
12. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
13. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
14. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137.
15. (a) Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051-1053.
16. (b) Lee, J. K.; Chi, Y. S.; Choi, I. S. Langmuir 2004, 20, 3844-3847.
17. (c) O'Reilly, R. K.; Joralemon, M. J.; Wooley, K. L.; Hawker, C. J. Chem. Mater. 2005, 17, 5976-5988.
18. (d) Fleming, D. A.; Thode, C. J.; Williams, M. E. Chem. Mater. 2006, 18, 2327-2334.
19. (e) Collman, J. P.; Devaraj, N. K.; Eberspacher, T. P. A.; Chidsey, C. E. D. Langmuir 2006, 22, 2457-2464.
20. Gheorge, A.; Matsuno, A.; Reiser, O. Adv. Synth. Catal. 2006, 348, 1016-1020.
21. Gissibi, A.; Finn, M. G.; Reiser, O. Org. Lett. 2005, 7, 2325-2328.
22. Font, D.; Jimeno, C.; Pericàs, M. A. Org. Lett. 2006, 8, 4653-4655.
23. Detz, R. J.; Arévalo Heras, S.; de Gelder, R.; van Leeuwen, P. W. N. M.; Hiemstra, H.; Reek, J. N. H.; van Maarseveen, J. H. Org. Lett. 2006, 8, 3227-3230.
24. The asymmetric reduction of a suitable diaryl ketone precursor is usually hampered by low ee's due to the steric and electronic similarities between both aryl groups, see, for instance: Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662 and references therein.
25. (a) Bolshan, Y.; Chen, C.-Y.; Chilenski, J. R.; Gosselin, F.; Mathre, D. J.; O'Shea, P. D.; Roy, A.; Tillyer, R. D. Org. Lett. 2004, 6, 111-114.
26. (b) El Ahmad, Y.; Maillet, P.; Laurent, E.; Talab, A.; Teste, J. F.; Cédat, M. J.; Fiez-Vandal, P. Y.; Dokhan, R.; Ollivier, R. Eur. J. Med. Chem. 1997, 32, 205-218.
27. (c) Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron: Asymmetry 1996, 7, 1263-1266.
28. (d) Stanchev, S.; Rakovska, R.; Berova, N.; Snatze, G. Tetrahedron: Asymmetry 1995, 6, 183-189.
29. (e) Toda, F.; Tanaka, K.; Koshiro, K. Tetrahedron: Asymmetry 1991, 2, 873-874.
30. (f) Meguro, K.; Aizawa, M.; Sohda, T.; Kawamatsu, Y.; Nagaoka, A. Chem. Pharm. Bull. 1985, 33, 3787-3797.
31. (a) Harms, A. F.; Nauta, W. T. J. Med. Pharm. Chem. 1960, 2, 57-77.
32. (b) Sperber, N.; Papa, D.; Schwenk, E.; Sherlock, M. J. Am. Chem. Soc. 1949, 71, 887-890.
33. For a review, see: Schmidt, F.; Stemmler, R. T.; Rudolph, J.; Bolm, C. Chem. Soc. Rev. 2006, 35, 454-470.
34. (a) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1999, 64, 7940-7956.
35. (b) Bolm, C.; Hermanns, N.; Claben, A.; Muñiz, K. Bioorg. Med. Chem. Lett. 2002, 12, 1795-1798.
36. Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1998, 63, 7078-7082.
37. Product specifications provided by the vendor (Novabiochem).
38. Harju, K.; Vahermo, M.; Mutikainen, I.; Yli-Kauhaluoma, J. J. Comb. Chem. 2003, 5, 826-833.
39. max.
40. Löber, S.; Gmeiner, P. Tetrahedron 2004, 60, 8699-8702.
41. 6 overnight before acquisition of the NMR spectra with the HRMAS probe.
42. Dosa, P. I.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444-445.
43. (a) Bolm, C.; Hermanns, N.; Hildebrand, J. P.; Muniz, K. Angew. Chem., Int. Ed. 2000, 39, 3465-3467.
44. (b) Bolm, C.; Kesselgruber, M.; Hermanns, N.; Hildebrand, J. P.; Raabe, G. Angew. Chem., Int. Ed. 2001, 40, 1488-1490.
45. Fontes, M.; Verdaguer, X.; Solà, L.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2004, 69, 2532-2543.
46. (a) Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124, 14850-14851.
47. (b) Rudolph, J.; Schmidt, F.; Bolm, C. Synthesis 2005, 840-842.
48. On the opposite side, when a low-loading resin (f = 0.29) prepared from a commercial Merrifield resin by reaction with defect sodium azide, capping with MeOH, and cycloaddition with amino alcohol 3a was used in the reaction, the enantiomeric purity of the resulting carbynol was 60 %. It is thus suggested that functionalization of the resin has an optimal value in the vicinity of f = 0.6 for this particular reaction.
49. Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124, 14850-14851.
50. For example, phenylation of p-tolualdehyde with a Merrifield resin substituted with (R)-2-piperazino-1,1,2-triphenylethanol as the ligand (5 %) furnishes the alcohol with 94% ee under similar conditions; see ref 5c.
51. Patwardhan, A. P.; Thompson, D. H. Langmuir 2000, 16, 10340-10350.
52. See, for instance: (a) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
53. (b) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327-6335.
54. (c) Kitamura, M.; Oka, H.; Noyori, R. Tetrahedron 1999, 55, 3605-3614.
55. (d) Rosner, T.; Sears, P. J.; Nugent, W. A.; Blackmond, D. G. Org. Lett. 2000, 2, 2511-2513.
56. (e) Goldfuss, B.; Steigelmann, M.; Khan, S. I.; Houk, K. N. J. Org. Chem. 2000, 65, 77-82.
57. (f) Vázquez, J.; Pericàs, M. A.; Maseras, F.; Lledós, A. J. Org. Chem. 2000, 65, 7303-7309.
58. (g) Rudolph, J.; Rasmussen, T.; Bolm, C.; Norrby, P. O. Angew. Chem., Int. Ed. 2003, 42, 3002-3005.
59. (h) Jimeno, C.; Vidal-Ferran, A.; Pericàs, M. A. Org. Lett. 2006, 8, 3895-3898.
60. (i) Rudolph, J.; Bolm, C.; Norrby, P. O. J. Am. Chem. Soc. 2005, 127, 1548-1552.
61. Spartan 02; Wavefuction, Inc.: Irvine, CA.