Chiral primary-tertiary diamine-brønsted acid salt catalyzed syn-selective cross-aldol reaction of aldehydes

Journal of Organic Chemistry

Volumn 75, Issue 13, 2010, Pages 4501-4507

  Li, Jiuyuan ^a   Fu, Niankai ^a   Li, Xin ^a   Luo, Sanzhong ^a   Cheng, Jin Pei ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACID SALTS; ALIPHATIC ALDEHYDES; CATALYTIC ACTIVITY; CROSS-ALDOL REACTION; GLYCOALDEHYDES; HIGH ACTIVITY; ISOBUTYRALDEHYDE; L-PHENYLALANINE; OPTIMAL CATALYSTS; PRIMARY AMINES; PROPIONALDEHYDE; SYN SELECTIVITY;

ACIDS; AMINO ACIDS; CATALYST SELECTIVITY; CONDENSATION REACTIONS;

ALDEHYDES;

ALDEHYDE; BRONSTED ACID; DIAMINE; ISOBUTYRALDEHYDE; PHENYLALANINE; PROPIONALDEHYDE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST;

EID: 77954135235     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100976e     Document Type: Article

References (71)

1. For reviews on direct aldol reactions, see: Modern Aldol Additions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004.
2. Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352-1374
3. Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65-75
4. Mukiyama, T. Angew. Chem., Int. Ed. 2004, 43, 5590
5. Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432-440
6. Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1997, 36, 1871
7. Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325-335
8. For reviews on chiral amine catalyzed direct aldol reactions, see: Dalko, P. L.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5176
9. Berkessel, A.; Groger, H. Asymmetric Organocatalysis: Wiley-VCH: Weinheim, 2005.
10. List, B. Acc. Chem. Res. 2004, 37, 548-557
11. List, B. Chem. Commun. 2006, 819-824
12. Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591
13. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569
14. Guillena, G.; Nájera, C.; Ramón, D. J. Tetrahedron: Asymmetry 2007, 18, 2249-2293
15. Geary, L. M.; Hultin, P. G. Tetrahedron: Asymmetry 2007, 20, 131-173
16. For leading examples, see: List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396
17. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267
18. Torri, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986
19. 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, 9285-9289
20. Córdova, A; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301
21. Aratake, S.; Itoh, T.; Okano, T.; Usui, T.; Shoji, M.; Hayashi, Y. Chem. Commun. 2007, 2524-2526
22. For examples of organocatalytic cross-aldol reaction of aldehydes, see: Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799
23. Pihko, P. M.; Erkkilä, A. Tetrahedron Lett. 2003, 44, 7607-7609
24. Chowdari, N. S.; Ramachary, D. B.; Córdova, A. Tetrahedron Lett. 2002, 43, 9591-9595
25. Casas, J.; Engqvist, M.; Ibrahem, I.; Kaynak, B.; Córdova, A. Angew. Chem., Int. Ed. 2005, 44, 1343-1345
26. Storer, R. I.; MacMillan, D. W. C. Tetrahedron 2004, 60, 7705-7714
27. Thayumanavan, R.; Tanaka, F.; Barbas, F. C., III. Org. Lett. 2004, 6, 3541-3544
28. Hayashi, Y.; Aratake, S.; Okano, T.; Takahashi, J.; Samiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2006, 45, 5527-5529
29. Mangion, I, K.; Northrup, A. B.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 6722-6724
30. Reyes, E.; Córdova, A. Tetrahedron. Lett. 2005, 46, 6605-6609
31. Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152-2154
32. Northrup, A. B.; Macmillan, D. W. C. Science 2004, 305, 1752-1755
33. Córdova, A.; Engqvist, M.; Ibrahem, I.; Casas, J.; Sundén, H. Chem. Commun. 2005, 2047-2049
34. Córdova, A.; Ibrahem, I.; Casas, J.; Sundén, H.; Engqvist, M.; Reyes, E. Chem. - Eur. J. 2005, 11, 4772-4784
35. Hayashi, Y.; Itoh, T.; Aratake, S.; Ishikawa, H. Angew. Chem., Int. Ed. 2008, 47, 2082-2084
36. Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420-2423
37. Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785
38. Mans, D. M.; Pearson, W. H. Org. Lett. 2004, 6, 3305
39. Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372
40. Kano, T.; Yamaguchi, Y.; Tanaka, Y.; Maruoka, K. Angew. Chem.,Int. Ed. 2007, 46, 1738-1741
41. Kano, T.; Yamaguchi, Y.; Maruoka, K. Chem. - Eur. J. 2009, 15, 6678-6687
42. For recent reviews for primary amine catalysis, see: Peng, F.; Shao, Z. J. Mol. Catal. A: Chem. 2008, 285, 1-13
43. Xu, L.-W.; Luo, J.; Lu, Y. Chem. Commun. 2009, 1807-1821
44. Xu, L.-W.; Lu, Y. Org. Biomol. Chem. 2008, 6, 2047-2053
45. Chen, Y.-C. Synlett. 2008, 1919
46. For selected examples on primary amines catalyzed direct aldol reactions, see: Córdova, A.; Zou, W.; Dziedzic, P.; Ibrahem, I.; Reyes, E.; Xu, Y. Chem. - Eur. J. 2006, 12, 5383-5397
47. Nakayama, K.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 17666-17667
48. Zhou, J.; Wakchaure, V.; Kraft, P.; List, B. Angew. Chem., Int. Ed. 2008, 47, 7656-7658
49. Li, J.; Yang, Z.; Wang, Z.; Wang, F.; Chen, X.; Liu, X.; Feng, X.-M. J. Am. Chem. Soc. 2008, 130, 5654-5655
50. For selected examples of primary amine catalyzed syn -aldol reaction of ketones, see: Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2007, 129, 288-289
51. Ramasastry, S. S. V.; Albertshofer, K.; Utsumi, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2007, 46, 5572-5575
52. Xu, X.-Y.; Wang, Y.-Z.; Gong, L.-Z. Org. Lett. 2007, 9, 4247-4249
53. Ramasastry, S. S. V.; Albershofer, K.; Utsumi, N.; Barbas, C. F., III. Org. Lett. 2008, 10, 1621-1624
54. Wu, X.; Ma, Z.; Ye, Z.; Qian, S.; Zhao, G. Adv. Synth. Catal. 2009, 351, 158-162
55. Luo, S.; Xu, H.; Li, J.; Zhang, L.; Cheng, J.-P. J. Am. Chem. Soc. 2007, 129, 3074-3075
56. Luo, S.; Xu, H.; Zhang, L.; Li, J.; Cheng, J.-P. Org. Lett. 2008, 10, 653-656
57. Luo, S.; Xu, H.; Chen, L.; Cheng, J.-P. Org. Lett. 2008, 10, 1775-1778
58. Li, J.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2009, 74, 1747-1750
59. Luo, S.; Qiao, Y.; Zhang, L.; Li, J.; Li, X.; Cheng, J.-P. J. Org. Chem. 2009, 74, 9521-9523
60. Markert, M.; Scheffler, U.; Mahrwald, R. J. Am. Chem. Soc. 2009, 131, 16642-16643
61. The reason why acetone and propionaldehyde perform quite differently remains an intriguing problem. Presumably this may be rationalized by considering the readily enolizable nature of propionaldehyde.
62. For discussions on water effect in enamine-based aldol reactions, see: Mlynarski, J.; Paradowska, J. Chem. Soc. Rev. 2008, 37, 1502-1511
63. Blackmond, D. G.; Armstrong, A.; Coombe, V.; Wells, A. Angew. Chem., Int. Ed. 2007, 46, 3798-3800
64. Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem., Int. Ed. 2006, 45, 8100-8102
65. For selected examples, see ref 3b and: Torri, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986
66. Zotova, N.; Franzke, A.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2007, 129, 15100
67. For selected examples on direct aldol reaction of glycol aldehyde, see: Garrabou, X.; Castillo, J. A.; Guérard-Hélaine, C.; Parella, T.; Joglar, J.; Lemaire, M.; Clapés, P. Angew. Chem., Int. Ed. 2009, 48, 5521-5525
68. Pizzarello, S.; Weber, A. L. Science 2004, 303, 1151
69. Kofoed, J.; Machuqueiro, M.; Reymond, J. L.; Barbre, T. Chem. Commun. 2004, 1540-1541
70. In several cases, the reduced aldol products were acetylated for purification.
71. Matsuno, J.; Iida, D.; Yamanaka, H.; Mukaiyama, T. Tetrahedron 2003, 59, 6739-6750