Organocatalytic asymmetric syn-aldol reactions of aldehydes with long-chain aliphatic ketones on Water and with dihydroxyacetone in organic solvents

Advanced Synthesis and Catalysis

Volumn 350, Issue 9, 2008, Pages 1390-1396

  Zhu, Ming Kui ^a,c   Xu, Xiao Ying ^a   Gong, Liu Zhu ^a,b  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Aldol reaction; Aqueous phase catalysis; Asymmetric catalysis; Carbohydrates; Hydrogen bonds; Organic catalysis

Indexed keywords

EID: 53849091309     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800105     Document Type: Article

References (53)

1. a) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615;
2. b) U. Eder, R. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492;
3. Angew. Chem. Int. Ed. Engl. 1971, 10, 496;
4. c) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395;
5. d) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260;
6. e) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386.
7. For reviews: a) B. List, Tetrahedron 2002, 58, 5573;
8. b) B. List, Synlett 2001, 1675;
9. c) B. Alcaide, P. Almendros, Angew. Chem. 2003, 115 884;
10. Angew. Chem. Int. Ed. 2003, 42, 858;
11. d) B. List, Acc. Chem. Res. 2004, 37, 548;
12. e) W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580;
13. f) S. Saito, H. Yamamoto, Acc. Chem. Res. 2004, 37, 570;
14. g) C. Palomo, M. Oiarbide, J. M. García, Chem. Soc. Rev. 2004, 33, 65;
15. h) Modern Aldol Reactions, Vols. 1 and 2, (Ed.: R. Mahrwald), Wiley-VCH, Weinheim, 2004;
16. i) S. Mukherjee, Y. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471;
17. j) G. Guillena, C. Najera, D. J. Ramon, Tetrahedron: Asymmetry 2007, 18, 2249.
18. S. Luo, H. Xu, J. Li, L. Zhang, J.-P. Cheng, J. Am. Chem. Soc. 2007, 129, 3074.
19. a) S. S. V. Ramasastry, H. Zhang, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2007, 129, 288;
20. b) T. Kano, Y. Yamaguchi, Y. Tanaka, K. Maruoka, Angew. Chem. 2007, 119, 1768;
21. Angew. Chem. Int. Ed. 2007, 46, 1738;
22. c) P. Diner, M. Amedjkouh, Org. Biomol. Chem. 2006, 4, 2091;
23. d) N. Utsumi, M. Imai, F. Tanaka, S. S. V. Ramasastry, C. F. Barbas III, Org. Lett. 2007, 9, 3445;
24. e) X. Wu, Z. Jiang, H.-M. Shen, Y. Lu, Adv. Synth. Catal. 2007, 349, 812.
25. For an excellent review, see: M. Markert, R. Mahrwald, Chem. Eur. J. 2008, 14, 40.
26. a) S. S. V. Ramasastry, K. Albertshofer, N. Utsumi, F. Tanaka, C. F. Barbas III, Angew. Chem. 2007, 119, 5668;
27. Angew. Chem. Int. Ed. 2007, 46, 5572;
28. b) after completion of this manuscript, a paper by Luo and Cheng concerning syn-aldol reaction of dihydroxyacetone published on the web: S. Luo, H. Xu, L. Zhang, J. Li, J.-P. Cheng, Org. Lett. 2008, 10, 653.
29. For the concept of the "on-water" reaction, see: S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. 2005, 117, 3339;
30. Angew. Chem. Int. Ed. 2005, 44, 3275.
31. 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;
32. 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;
33. c) Z. Tang, Z.-H. Yang, X.-H. Chen, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, J. Am. Chem. Soc. 2005, 127, 9285;
34. d) X.-Y. Xu, Y.-Z. Wang, L.-F. Cun, L.-Z. Gong, Tetrahedron: Asymmetry 2007, 18, 237;
35. e) X.-H. Chen, S.-W. Luo, Z. Tang, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Chem. Eur. J. 2007, 13, 689;
36. f) L. He, Z. Tang, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Tetrahedron 2006, 62, 346.
37. X.-Y. Xu, Y.-Z. Wang, L.-Z. Gong, Org. Lett. 2007, 9, 4247.
38. For recent reports and discussions on the aldol reactions in aqueous media, see: a) N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 734;
39. b) Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. 2006, 118, 972;
40. Angew. Chem. Int. Ed. 2006, 45, 958;
41. c) Y. Hayashi, S. Aratake, T. Okano, J. Takahashi, T. Sumiya, M. Shoji, Angew. Chem. 2006, 118, 5653;
42. Angew. Chem. Int. Ed. 2006, 45, 5527;
43. d) A. P. Brogan, T. J. Dickerson, K. D. Janda, Angew. Chem. 2006, 118, 8278;
44. Angew. Chem. Int. Ed. 2006, 45, 8100;
45. e) Y. Hayashi, Angew. Chem. 2006, 118, 8281;
46. Angew. Chem. Int. Ed. 2006, 45, 8103;
47. f) J. Huang, X. Zhang, D. W. Armstrong, Angew. Chem. 2007, 119, 9231;
48. Angew. Chem. Int. Ed. 2007, 46, 9073.
49. a) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966;
50. b) V. Maya, M. Raj, V. K. Singh, Org. Lett. 2007, 9, 293.
51. Y.-R. Shen, V. Ostroverkhov, Chem. Rev. 2006, 106, 1140.
52. a) Y. Jung, R. A. Marcus, J. Am. Chem. Soc. 2007, 129, 5492;
53. b) J. Chandrasekhar, S. Shariffskul, W. L. Jørgensen, J. Phys. Chem. B. 2002, 106, 8078.