A selective direct aldol reaction in aqueous media catalyzed by zinc-proline

European Journal of Organic Chemistry

Volumn , Issue 24, 2005, Pages 5268-5276

  Fernandez Lopez, Ruben ^a   Kofoed, Jacob ^a   Machuqueiro, Miguel ^a   Darbre, Tamis ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

Aldol reactions; Aqueous catalysis; Green chemistry; Proline; Zinc

Indexed keywords

EID: 30044448417     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500352     Document Type: Article

References (55)

1. For review articles and references, see: a) T. D. Machajewski, C.-H. Wong, Angew. Chem. Int. Ed. 2000, 39, 1352-1375;
2. b) C. Palomo, M. Oiarbide, J. M. Garcia, Chem. Eur. J. 2002, 5, 36;
3. c) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389;
4. d) H. Gröger, E. M. Vogl, M. Shibasaki, Chem. Eur. J. 1998, 4, 1137-1141.
5. a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396;
6. b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387;
7. c) B. List, Tetrahedron 2002, 58, 5573-5590;
8. d) L. Hoang, S. Bahmanyar, B. List, J. Am. Chem. Soc. 2003, 125, 16-17;
9. e) D. W. C. MacMillan, A. B. Northrup, J. Am. Chem. Soc. 2002, 124, 6798;
10. f) K. Sakthievel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267.
11. a) Z. Tang, F. Jiang, L.-T. Yu, X. Cui, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Y.-D. Wu, J. Am. Chem. Soc. 2003, 125, 5262-5263;
12. b) Z. Tang, F. Jiang, X. Cui, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Y-D. Wu, Proc. Natl. Acad. Sci. USA 2004, 101, 5755;
13. c) H. J. Martin, B. List, Synlett 2003, 1901;
14. d) J. Kofoed, J. Nielsen, J.-L. Reymond, Bioorg. Med. Chem. Lett. 2003, 13, 2445.
15. a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873;
16. b) N. Yoshikawa, Y. M. A. Yamada, J. Das, M. Sasai, H. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168-4178;
17. c) N. Kumagai, S. Matsunaga, N. Yoshikawa, T. Ohshima, M. Shibasaki, Org. Lett. 2001, 3, 1539-1542.
18. a) B. M. Trost, H. Ito, J. Am. Chem. Soc. 2004, 122, 12003-12004;
19. b) B. M. Trost, E. R. Silcoff, H. Ito, Org. Lett. 2001, 3, 2497-2500;
20. c) B. M. Trost, H. Ito, E. R. Silcoff, J. Am. Chem. Soc. 2001, 123, 3367-3368.
21. a) C.-H. Wong, G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994;
22. b) H. J. M. Gijsen, L. Qiao, W. Fitz, C.-H. Wong, Chem. Rev. 1996, 96, 443-476.
23. a) J. Wagner, C. F. Barbas III, R. A. Lerner, Science 1995, 270, 1797-1800;
24. b) T. Hoffmann, G. Zhong, B. List, D. Shabat, J. Anderson, S. Gramatikova, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 1998, 120, 2768-2779;
25. c) B. List, D. Shabat, G. Zhong, J. M. Turner, A. Li, T. Bui, J. Anderson, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 1999, 121, 7283-7291;
26. d) G. Zhong, R. A. Lerner, C. F. Barbas III, Angew. Chem. Int. Ed. 1999, 38, 3738-3741.
27. A. Córdova, C. F. Barbas III, W. Notz, Chem. Commun. 2002, 3024-3025.
28. T. J. Dickerson, K. D. Janda, J. Am. Chem. Soc. 2002, 124, 3220-3221.
29. Y.-Z. Jiang, Z. Tang, Z.-H. Yang, L.-F. Cun, L.-Z. Gong, A.-Q. Mi, Org. Lett. 2004, 6, 2285-2287.
30. a) P. M. Pihko, A. I. Nyberg, A. Usano, Synlett 2004, 11, 1891-1896;
31. b) V. Jheengut, D. E. Ward, Tetrahedron Lett. 2004, 45, 8347-8350.
32. P. I. Arvidsson, A. Hartikka, Tetrahedron: Asymmetry 2004, 15, 1831-1834.
33. a) S. Kobayashi, Chem. Eur. J. 2002, 8, 4094;
34. b) S. Kobayashi, K. Manabe, Acc. Chem. Res. 2002, 35, 209-217.;
35. c) S. Kobayashi, T. Hamada, S. Nagayama, K. Manabe, Org. Lett. 2001, 3, 165;
36. d) S. Kobayashi, S. Nagayama, T. Busujima, Tetrahedron 1999, 55, 8739;
37. e) S. Nagayama, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 11531;
38. f) T. Hamada, K. Manabe, S. ishikawa, S. Nagayama, M. Shiro, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 2989-2996.
39. For selected reviews on stereoselective organic reactions in water, see: a) U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772;
40. b) D. Sinou, Adv. Chem. Catal. 2002, 344, 221-237.
41. T. Darbre, M. Machuqueiro, Chem. Commun. 2003, 1090-1091.
42. a) J. Kofoed, M. Machuqueiro, J.-L. Reymond, T. Darbre, Chem. Commun. 2004, 1540-1541;
43. b) J. Kofoed, J.-L. Reymond, T. Darbre, Org. Biol. Chem. 2005, 1850-1855.
44. S. Kobayashi, S. Nagayama, T. Busujima, J. Am. Chem. Soc. 1998, 120, 8287-8288.
45. M. T. Konieczny, P. H. Toma, M. Cushiman, J. Org. Chem. 1993, 58, 4619.
46. A syn/anti ratio of 4:1 has been reported for the same reaction under our conditions: Y-S. Wu, W.-Y. Shao, C.-Q. Zheng, Z.-L. Huang, J. Cai, Q.-Y. Deng, Helv. Chim. Acta 2004, 87, 1377-1383.
47. B. List, D. Shabat, C. F.Barbas III, R. A. Lerner, Chem. Eur. J. 1998, 881-885.
48. [11] is that water hydrolyzes the oxazolidone formed from proline and aldehydes, thus regenerating the catalyst.
49. 1H NMR spectroscopy and mass spectrometry.
50. R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882-2883.
51. I. Stahl, F. Wrabletz, J. Gosselck, Chem. Ber. 1989, 122, 371-375.
52. M. A. Joy, J. S. Paver, M. B. Hursthouse, Chem. Commun. 2002, 18, 2150-2151.
53. B. M. Choudary, M. L. Kantam, B. Kavita, C. V. Rao, K. K. Reddy, F. Figueras, Tetrahedron. Lett. 1998, 38, 3555-3558.
54. C. Le Roux, M. Maraval, M. E. Borredon, H. Dubac, J. Gaspard-Iloughmane, Tetrahedron Lett. 1992, 33, 1053-1054.
55. A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319-9320.