Merrifield resin supported dipeptides: Efficient and recyclable organo-catalysts for asymmetric aldol reactions under neat reaction conditions

Synthesis

Volumn , Issue 13, 2008, Pages 2065-2072

  Yan, Jincan ^a   Wang, Lei ^a,b  

^a Department of Chemistry   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aldol reaction; Merrifield resin; Neat reaction conditions; Organocatalyst; Peptide

Indexed keywords

ALDEHYDES; CATALYST ACTIVITY; CATALYSTS; ENANTIOSELECTIVITY; KETONES; ORGANIC COMPOUNDS; RESINS;

ALDOL REACTIONS; ASYMMETRIC ALDOL REACTIONS; CATALYTIC ACTIVITIES; CATALYTIC AMOUNTS; DI-PEPTIDES; DIASTEREOSELECTIVITIES; ENANTIOSELECTIVITIES; ISOLATED YIELDS; MERRIFIELD RESINS; REACTION CONDITIONS; ROOM-TEMPERATURE (RT); TRI PEPTIDES;

CATALYSIS;

2 [(2 CHLORO 5 NITROPHENYL)(HYDROXY)METHYL]CYCLOHEXANONE; 2 [(4 CHLORO 3 NITROPHENYL)(HYDROXY)METHYL]CYCLOHEXANONE; 2 [(4 CYANOPHENYL)(HYDROXY)METHYL]CYCLOHEXANONE; 2 [HYDROXY (1 NAPHTHYL)METHYL]CYCLOHEXANONE; 2 [HYDROXY (2 NAPHTHYL)METHYL]CYCLOHEXANONE; 2 [HYDROXY (4 NITROPHENYL)METHYL]CYCLOPENTANONE; 2 [HYDROXY(2 NITROPHENYL)METHYL]CYCLOHEXANONE; 2 [HYDROXY(3 NITROPHENYL)METHYL]CYCLOHEXANONE; 2 [HYDROXY(4 NITROPHENYL)METHYL]CYCLOHEXANONE; 2 [HYDROXY(PHENYL)METHYL]CYCLOHEXANONE; 2 [HYDROXY[4 (TRIFLUOROMETHYL)PHENYL]METHYL]CYCLOHEXANONE; 3 [HYDROXY (4 NITROPHENYL)]METHYL]TETRAHYDROTHIOPYRAN 4 ONE; 3,4 DIHYDROXY 4 (4 NITROPHENYL)BUTAN 2 ONE; 4 HYDROXY 4 (4 NITROPHENYL)BUTAN 2 ONE; ALDEHYDE; DIPEPTIDE; KETONE; RESIN; TRIPEPTIDE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOMER; ENANTIOSELECTIVITY; RECYCLING; ROOM TEMPERATURE;

EID: 47349091310     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067104     Document Type: Article

References (65)

1. (a) Mukaiyama, T. Tetrahedron 1999, 55, 8609.
2. (b) Nicolaou, K. C.; Vourloumis, D.; Wissinger, N.; Baran, P. S. Angew. Chem. Int. Ed. 2000, 39, 44.
3. (c) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448.
4. (d) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233.
5. (e) Keck, G. E.; Wager, C. A.; Sell, T.; Wager, T. T. J. Org. Chem. 1999, 64, 2172.
6. (a) Scheidt, K. A.; Bannister, T. D.; Tasaka, A.; Wendt, M. D.; Savall, B. M.; Fegley, G. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 6981.
7. (b) White, J. D.; Blakemore, P. R.; Green, N. J.; Hauser, E. B.; Holoboski, M. A.; Keown, L. E.; Kolz, C. S. N.; Phillips, B. W. J. Org. Chem. 2002, 67, 7750.
8. (c) Gerber-Lemaire, S.; Vogel, P. Eur. J. Org. Chem. 2003, 2959.
9. (a) Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991.
10. (b) Mahrwald, R. Modern Aldol Reactions, Vols. 1 and 2; Wiley-VCH: Weinheim, 2004.
11. For pioneering work using proline as a catalyst, see: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
12. (b) Eder, U.; Sauer, R.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496.
13. (c) List, B.; Lerner, R. A.; Barbas, C. F. III J. Am. Chem. Soc. 2000, 122, 2395.
14. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F. III J. Am. Chem. Soc. 2001, 123, 5260.
15. (e) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386. For reviews on direct aldol reactions catalyzed by secondary amine-based organic molecules, see:
16. (f) List, B. Acc. Chem. Res. 2004, 37, 548.
17. (g) Notz, W.; Tanaka, F.; Barbas, C. F. III Acc. Chem. Res. 2004, 37, 580.
18. (h) Saito, S.; Yamamoto, H. Acc. Chem. Res. 2004, 37, 570.
19. (i) List, B. Chem. Commun. 2006, 819.
20. (a) Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A.; Celentano, G. Adv. Synth. Catal. 2002, 344, 533.
21. (b) Shen, Z.-X.; Chen, W.-H.; Jiang, H.; Ding, Y.; Luo, X.-Q.; Zhang, Y.-W. Chirality 2005, 17, 119.
22. (c) Gruttadauria, M.; Riela, S.; Aprile, C.; Meo, P. L.; D'Anna, F.; Noto, R. Adv. Synth. Catal. 2006, 348, 82.
23. (d) Bellis, E.; Kokotos, G. Tetrahedron 2005, 61, 8669.
24. (a) Berkessel, A.; Koch, B.; Lex, J. Adv. Synth. Catal. 2004, 346, 1141.
25. (b) Hartikka, A.; Arvidsson, P. I. Tetrahedron: Asymmetry 2004, 15, 1831.
26. (c) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem. Int. Ed. 2004, 43, 1983.
27. (d) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167.
28. (e) Kano, T.; Takai, J.; Tokuda, O.; Maruoka, K. Angew. Chem. Int. Ed. 2005, 44, 3055.
29. (f) Kano, T.; Tokuda, O.; Maruoka, K. Tetrahedron Lett. 2006, 47, 7423.
30. (g) Mitsumori, S.; Zhang, H.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F. Iii J. Am. Chem. Soc. 2006, 128, 1040.
31. (a) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755.
32. (b) Tang, Z.; Yang, Z.-H.; Chen, X.-H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. J. Am. Chem. Soc. 2005, 127, 9285.
33. (a) Chen, J.-R.; Lu, H.-H.; Li, X.-Y.; Chen, L.; Wan, J.; Xiao, W.-J. Org. Lett. 2005, 7, 4543.
34. (b) Chimni, S. S.; Mahajan, D.; Suresh, B. V. V. Tetrahedron Lett. 2005, 46, 5617.
35. (c) Gryko, D.; Lipinski, R. Adv. Synth. Catal. 2005, 347, 1948.
36. (d) Córdova, A.; Zou, W.-B.; Ibrahem, I.; Reyes, E.; Engqvist, M.; Liao, W.-W. Chem. Commun. 2005, 3586.
37. (e) Samanta, S.; Liu, J.-Y.; Dodda, R.; Zhao, C.-G. Org. Lett. 2005, 7, 5321.
38. (f) Cheng, C.-L.; Sun, J.; Wang, C.; Zhang, Y.; Wei, S.-Y.; Jiang, F.; Wu, Y.-D. Chem. Commun. 2006, 215.
39. (a) Kofoed, J.; Nielsen, J.; Reymond, J. L. Bioorg. Med. Chem. Lett. 2003, 13, 2445.
40. (b) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
41. (c) Tang, Z.; Yang, Z.-H.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Org. Lett. 2004, 6, 2285.
42. (d) Luppi, G.; Cozzi, G.; Monari, M.; Kaptein, B.; Broxterman, Q. B.; Tomasin, C. J. Org. Chem. 2005, 70, 7418.
43. (e) Krafttger, P.; Kovasy, R.; Revell, J. D.; Ivan, S.; Wennermers, H. Org. Lett. 2005, 7, 1101.
44. (f) Revell, J. D.; Gantenbein, D.; Krattigei, P.; Wennermers, H. Biopolymer 2006, 84, 105. (g) Zou, W.-B.; Ibrahem, I.; Dziedzic, P.; Sunden, H.; Córdova, A. Chem. Commun. 2005, 4946.
45. (h) Cordova, A.; Zou, W.-B.; Dziedzic, P.; Ibrahem, I.; Reyes, E.; Xu, Y. Chem. Eur. J. 2006, 12, 5383.
46. (i) Dziedzic, P.; Zou, W.-B.; Hafren, J.; Córdova, A. Org. Biomol. Chem. 2006, 4, 38.
47. (j) Tsogoeva, S. B.; Wei, S. W. Tetrahedron: Asymmetry 2005, 16, 1947.
48. (k) Tsogoeva, S. B.; Jagtap, S. B.; Ardemasova, Z. A. Tetrahedron: Asymmetry 2006, 17, 989.
49. Andreae, M. R. M.; Davis, A. P. Tetrahedron: Asymmetry 2005, 16, 2487.
50. (a) Benaglia, M.; Celentano, G.; Cozzi, F. Adv. Synth. Catal. 2001, 343, 171.
51. (b) Calderon, F.; Fernandez, R.; Sanchez, F.; Fernandez-Mayoralas, A. Adv. Synth. Catal. 2005, 347, 1395.
52. (c) Miao, W.-S.; Chan, T. H. Adv. Synth. Catal. 2006, 348, 1711.
53. (d) Zhou, L.; Wang, L. Chem. Lett. 2007, 36, 628.
54. Akagawa, K.; Sakamoto, S.; Kudo, K. Tetrahedron Lett. 2005, 46, 8185.
55. (a) Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F. III J. Am. Chem. Soc. 2006, 128, 734.
56. (b) Luo, S.-Z.; Xu, H.; Li, J.-Y.; Zhang, L.; Cheng, J.-P. J. Am. Chem. Soc. 2007, 129, 3074.
57. (c) Chen, J.-R.; Li, X.-Y.; Xing, X.-N.; Xiao, W.-J. J. Org. Chem. 2006, 71, 8198.
58. (a) Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem. Int. Ed. 2006, 45, 8100.
59. (b) Hayashi, Y. Angew. Chem. Int. Ed. 2006, 45, 8103.
60. (c) Blackmond, D. G.; Armstrong, A.; Coombe, V.; Wells, A. Angew. Chem. Int. Ed. 2007, 46, 3798.
61. Oskar, K.; Walter, E. K.; Gert, L.; Gemot, W.; Thomas, G.; Mark, A. S.; Clayton, H. H. Org. Synth. Coll. Vol. VII; John Wiley & Sons: London, 1990, 70.
62. Lei, M.; Shi, L.-X.; Li, G.; Chen, S.-L.; Fang, W.-H.; Ge, Z.-M.; Cheng, T.-M.; Li, R.-T. Tetrahedron 2007, 63, 7892.
63. Carrea, G.; Ottolina, G.; Lazcano, A.; Pironti, V.; Colonna, S. Tetrahedron: Asymmetry 2007, 18, 1265.
64. Gruttadauria, M.; Giacalone, F.; Mossuto Marculescu, A.; Lo Meo, P.; Riela, S.; Noto, R. Eur. J. Org. Chem. 2007, 28, 4688.
65. Gu, Q.; Wang, X.-F.; Wang, L.; Wu, X.-Y.; Zhou, Q.-L. Tetrahedron: Asymmetry 2006, 17, 1537.