Direct organocatalytic asymmetric aldol reactions of α-amino aldehydes: Expedient syntheses of highly enantiomerically enriched anti-β-hydroxy-α-amino acids

Organic Letters

Volumn 6, Issue 20, 2004, Pages 3541-3544

  Thayumanavan, Rajeswari ^a   Tanaka, Fujie ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; ALDEHYDE DERIVATIVE; AMINO ACID DERIVATIVE; TETRAZOLE DERIVATIVE;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

ALDEHYDES; AMINO ACIDS; CATALYSIS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 6444239481     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0485417     Document Type: Article

References (61)

1. (a) McDonald, L. A.; Barbieri, L. R.; Carter, G. T.; Lenoy, E.; Lotvin, J. J. Am. Chem. Soc. 2002, 124, 10260.
2. (b) Umezawa, K.; Nakazawa, K.; Ikeda, Y.; Nakagawa, H.; Kondo, S. J. Org. Chem. 1999, 64, 3034.
3. (c) Taniguchi, M.; Suzumura, K.; Nagai, K.; Kawasaki, T.; Saito, T.; Takasaki, J.; Suzuki, K.; Fujita, S.; Tsukamoto, S. Tetrahedron 2003, 59, 4533.
4. (d) Ford, P. W.; Gustafson, K. R.; McKee, T. C.; Shigematsu, N.; Maurizi, L. K.; Pannell, L. K.; Williams, D. E.; de Silva, E. D.; Lassota, P.; Allen, T. M.; Soest, R. V.; Andersen, R. J.; Boyd, M. R. J. Am. Chem. Soc. 1999, 121, 5899.
5. (a) Saravanan, P.; Corey, E. J. J. Org. Chem. 2003, 68, 2760.
6. (b) Jackson, B. G.; Pedersen, S. W.; Fisher, J. W.; Misner, J. W.; Gardner, J. P.; Staszak, M. A.; Doecke, C.; Rizzo, J.; Aikins, J.; Farkas, E.; Trinkle, K. L.; Vicenzi, J.; Reinhard, M.; Kroeff, E. P.; Higginbotham, C. A.; Gazak, R. J.; Zhang, T. Tetrahedron 2000, 56, 5667.
7. (c) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709.
8. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584.
9. (e) Panek, J. S.; Masse. C. E. J. Org. Chem. 1998, 63, 2382.
10. (a) Makino, K.; Goto, T.; Hiroki, Y.; Haniada, Y. Angew. Chem., Int. Ed. 2004, 43, 882.
11. (b) Mordant, C.; Dunkelmann, P.; Ratovelomanana-Vidal, V.; Genet, J.-P. Chem. Commun. 2004, 1296.
12. (c) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542.
13. (d) Yoshikawa, N.; Shibasaki, M. Tetrahedron 2002, 58, 8289 and references therein,
14. (e) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
15. (f) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884.
16. (g) Kobayashi, J.; Nakamura, M.; Mori, Y.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 9192.
17. (h) Ooi, T.; Kamada, M.; Taniguchi, M.; Maruoka, J. Am. Chem. Soc. 2004, 126, 9685.
18. (a) Silvestri, M. G.; Desantis, G.; Michell, M.; Wong, C.-H. Top. Stereochem. 2003, 23, 267.
19. (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734.
20. (c) Tanaka, F.; Oda, M.; Fujii, I. Tetrahedron Lett. 1998, 39, 5057.
21. Reviews: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (b) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (c) Altermann, C.; Gordillo. R.; Clemente, F.; Cheong, P. H.-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558. (d) Note, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
22. Reviews: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (b) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (c) Altermann, C.; Gordillo. R.; Clemente, F.; Cheong, P. H.-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558. (d) Note, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
23. Reviews: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (b) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (c) Altermann, C.; Gordillo. R.; Clemente, F.; Cheong, P. H.-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558. (d) Note, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
24. Reviews: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (b) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (c) Altermann, C.; Gordillo. R.; Clemente, F.; Cheong, P. H.-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558. (d) Note, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
25. (a) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152.
26. (b) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983.
27. (c) Hartikka, A.; Arvidsson, P. I. Tetrahedron: Asymmetry 2004, 15, 1831.
28. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jorgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790.
29. (e) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 726, 4108.
30. (f) Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317.
31. (g) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 725, 10808.
32. (h) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247.
33. Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374.
34. (J) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558.
35. (a) Joly, G. D.; Jacobsen, E. N. J. Am. Chem, Soc. 2004, 126, 4102.
36. (b) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 725, 12672.
37. (c) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
38. (d) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
39. (e) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Proc. Natl, Acad. Sci. U.S.A. 2004, 101, 5846.
40. (f) Denmark, S. E.; Bui, T. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5439.
41. (a) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420.
42. (b) Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369.
43. (c) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301.
44. (d) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591.
45. (e) Sakthivel, K.; Notz, N.; Bui, T.; C. F. Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260.
46. (a) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, 6, 2507.
47. (b) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III. J. Org. Chem. 2003, 68, 9624.
48. (c) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866.
49. (d) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906.
50. (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 1509.
51. (b) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527.
52. (c) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737.
53. Palucki, M.; Hughes, D. H.; Yasuda, N.; Yang, C.; Reider, P. J. Tetrahedron Lett. 2001, 42, 6811.
54. (a) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757.
55. (b) Williams, L.; Zhang, Z.; Shao, F.; Carroll, P. J.; Joullie, M. M. Tetrahedron 1996, 52, 11673.
56. (c) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181.
57. (d) Kanemasa, S.; Mori, A.; Tatsukawa, A. Tetrahedron Lett. 1993, 34, 8293.
58. (e) Corey, E. J.; Lee, D.-H.; Choi, S. Tetrahedron Lett. 1992, 33, 6735.
59. (f) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34.
60. Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249.
61. Diastereomeric ratio of the aldol products decreased by epimerization at C2 when they were stored or when they were purified by silica gel column chromatography. See refs 9b,c. Column chromatography did not completely separate the anti and syn isomers of 3.