Current progress in the asymmetric aldol addition reaction

Chemical Society Reviews

Volumn 33, Issue 2, 2004, Pages 65-75

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   García, Jesús M ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CARBON; CARBONYL DERIVATIVE; LEWIS ACID; METAL COMPLEX; ORGANIC COMPOUND; REAGENT; SILANE DERIVATIVE;

ADDITION REACTION; ALDOL REACTION; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHIRALITY; COVALENT BOND; MUKAIYAMA REACTION; ORGANIC CHEMISTRY; QUANTITATIVE ANALYSIS; QUANTUM YIELD; REACTION ANALYSIS; REVIEW; SILYLATION; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 1642386775     PISSN: 03060012     EISSN: 14604744     Source Type: Journal    
DOI: 10.1039/b202901d     Document Type: Article

References (57)

1. M. Braun, in Stereoselective Synthesis, Houben-Weyl, Vol. E21/3, Eds. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme, Stuttgart, 1996, p. 1603
2. C. J. Cowden, I. Paterson, Org. React., 1997, 51, 1
3. R. Mahrwald, Chem. Rev., 1999, 99, 1095
4. S. G. Nelson, Tetrahedron: Asymmetry, 1998, 357
5. E. M. Carreira, in Comprehensive Asymmetric Catalysis, Vol. 3, Eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Heildelberg, 1999, pp. 997-1065
6. D. Machajewski, C.-H. Wong, Angew. Chem. Int. Ed., 2000, 39, 1352
7. B. Alcaide, P. Almendros, Eur. J. Org. Chem., 2002, 1595
8. C. Palomo, M. Oiarbide, J. M. García, Chem. Eur. J., 2002, 8, 36
9. I. Paterson, T. Temal-Laïb, Org. Lett., 2002, 4, 2473
10. I. Paterson, C. J. Cowden, D. J. Wallace, in Modern Carbonyl Chemistry; Ed. J. Otera, Wiley-VCH, Weinheim, 2000, pp. 249-297
11. J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995
12. D. A. Evans, Aldrichimica Acta, 1982, 15, 23
13. M. T. Crimmins, B. W. King, E. A. Tabet, J. Am. Chem. Soc., 1997, 119, 7883
14. D. A. Evans, C. W. Downey, J. T. Shaw, J. S. Tedrow, Org. Lett., 2002, 4, 1127
15. A. Abiko, J.-F. Liu, S. Masamune, J. Am. Chem. Soc., 1997, 119, 2586
16. M. Braun, Angew. Chem. Int. Ed. Engl., 1987, 26, 24
17. M. Braun, S. Graf, Org. Synth., 1998, 9, 497
18. S. Saito, K. Hatanaka, T. Kano, H. Yamamoto, Angew. Chem. Int. Ed., 1998, 37, 3378
19. C. Palomo, A. González, J. M. García, C. Landa, M. Oiarbide, S. Rodríguez, A. Linden, Angew. Chem. Int. Ed., 1998, 37, 180
20. A. Abiko, T. Inoue, H. Furuno, H. Schwalde, C. Fieres, S. Masamune, J. Am. Chem. Soc., 2001, 123, 4605
21. N. Iwasawa, T. Mukaiyama, Chem. Lett., 1982, 1441
22. T. Mukaiyama, S. Kobayashi, H. Uchiro, I. Shiina, Chem. Lett., 1990, 129
23. S. Kobayashi, T. Mukaiyama, in Stereocontrolled Organic Synthesis, Ed. B. M. Trost, Blackwell, Cambridge, 1994, pp. 37-65
24. T. Ooi, K. Doda, K. Maruoka, Org. Lett., 2001, 3, 1273
25. E. M. Carreira, R. A. Singer, W. S. Lee, J. Am. Chem. Soc., 1994, 116, 8837
26. Y. Yamashita, H. Ishitani, H. Shimizu, S. Kobayashi, J. Am. Chem. Soc., 2002, 124, 3292
27. D. A. Evans, C. S. Burgey, M. C. Koxlowski, S. W. Tregay, J. Am. Chem. Soc., 1999, 121, 686
28. K. Oisaki, Y. Suto, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2003, 125, 5644
29. U. M. Lindström, Chem. Rev., 2002, 102, 2751
30. T. Hamada, K. Manabe, S. Ishikawa, S. Nagayama, M. Shiro, S. Kobayashi, J. Am. Chem. Soc., 2003, 125, 1989
31. H.-J. Li, H.-Y. Tian, Y.-J. Chen, D. Wang, C. J. Li, Chem. Commun., 2002, 2994
32. C.-T. Chen, S.-D. Chao, K.-C. Yen, C.-H. Chen, I.-C. Chou, S.-W. Hon, J. Am. Chem. Soc., 1997, 119, 11341
33. S. E. Denmark, R. A. Stavenger, Acc. Chem. Res., 2000, 33, 432
34. S. E. Denmark, S. K. Ghosh, Angew. Chem. Int. Ed., 2001, 40, 4759
35. S. E. Denmark, Y. Fan, J. Am. Chem. Soc., 2002, 124, 4233
36. M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun., 2002, 1989
37. N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguzhi, M. Shibasaki, J. Am. Chem. Soc., 2003, 125, 2169
38. B. M. Trost, H. Ito, E. R. Shilcoff, J. Am. Chem. Soc., 2001, 123, 3367
39. W. Yao, J. Wang, Org. Lett., 2003, 5, 1527
40. R. Mahrwald, B. Ziemer, Tetrahedron Lett., 2002, 43, 4459
41. R. Mahrwald, Org. Lett., 2000, 2, 4011
42. D. A. Evans, C. W. Downey, J. L. Hubbs, J. Am. Chem. Soc., 2003, 125, 8706
43. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc., 2000, 122, 2395
44. W. Notz, B. List, J. Am. Chem. Soc., 2000, 122, 7386
45. K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc., 2001, 123, 5260
46. L. Hoang, S. Bahmanyar, K. N. Houk, B. List, J. Am. Chem. Soc., 2003, 125, 16
47. S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc., 2003, 125, 2475
48. 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
49. B. Alcaide, P. Almendros, Angew. Chem. Int. Ed., 2003, 42, 858
50. N. S. Chowdari, D. B. Ramachary, A. Córdova, C. F. Barbas III, Tetrahedron Lett., 2002, 43, 9591
51. A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun., 2002, 620
52. C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. Int. Ed., 2003, 42, 2785
53. A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc., 2002, 124, 6798
54. M. Nakadai, S. Saito, H. Yamamoto, Tetrahedron, 2002, 58, 8167
55. T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. Int. Ed., 2002, 41, 4542
56. A. Córdova, W. Notz, C. F. Barbas III, Chem. Commun., 2002, 3024
57. T. J. Dickerson, K. D. Janda, J. Am. Chem. Soc., 2002, 124, 3220