One-pot synthesis of chiral α-substituted β,γ-epoxy aldehyde derivatives through an asymmetric aldol reaction of chloroacetaldehyde

Angewandte Chemie - International Edition

Volumn 50, Issue 12, 2011, Pages 2804-2807

  Hayashi, Yujiro ^a   Yasui, Yusuke ^a   Kawamura, Tsuyoshi ^a   Kojima, Masahiro ^a   Ishikawa, Hayato ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

aldol reaction; asymmetric synthesis; diarylprolinol derivatives; epoxidation; organocatalysis

Indexed keywords

ALDOL REACTIONS; ASYMMETRIC ALDOL REACTIONS; ASYMMETRIC SYNTHESIS; CHLOROACETALDEHYDE; DIARYLPROLINOL DERIVATIVES; EPOXY ALDEHYDES; GOOD YIELD; KEY REACTIONS; ONE POT; ONE-POT SYNTHESIS; ORGANOCATALYSIS; SEQUENTIAL REACTION; SYNTHETIC PROCEDURES;

ALDEHYDES; CATALYSIS; CONDENSATION REACTIONS; ENANTIOSELECTIVITY; RATE CONSTANTS; REACTION KINETICS;

SYNTHESIS (CHEMICAL);

EID: 79952520858     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201005577     Document Type: Article

References (69)

1. Comprehensive Asymmetric Catalysis (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Heidelberg, 1999.
2. T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974.
3. W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. 1990, 112, 2801.
4. R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki, Tetrahedron Lett. 1990, 31, 7345.
5. Y. Shi, Acc. Chem. Res. 2004, 37, 488.
6. W. Zhang, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 286, and references therein.
7. Selected references
8. H. Kakei, R. Tsuji, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 8962
9. M. Marigo, J. Franzen, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964
10. C. A. Lattanzi, Chem. Commun. 2009, 1452
11. O. Lifchits, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2010, 132, 10227.
12. S. Arai, T. Shioiri, Tetrahedron Lett. 1998, 39, 2145
13. P. Bakõ, K. Vizárdi, Z. Bajorm, L. Tõke, Chem. Commun. 1998, 1193
14. V. K. Aggarwal, J. P. H. Charmant, D. Fuentes, J. N. Harvey, G. Hynd, D. Ohara, W. Picoul, C. Smith, J.-L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2006, 128, 2105.
15. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395.
16. For selected reviews on organocatalysis, see
17. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248
18. Angew. Chem. Int. Ed. 2004, 43, 5138
19. Asymmetric Organocatalysis (Eds.:, A. Berkessel, H. Groger,), Wiley-VCH, Weinheim, 2005
20. Y. Hayashi, J. Synth. Org. Chem. Jpn. 2005, 63, 464
21. B. List, Chem. Commun. 2006, 819
22. M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001
23. M. J. Gaunt, C. C. C. Johansson, A. McNally, N. T. Vo, Drug Discovery Today 2007, 12, 8
24. Enantioselective Organocatalysis (Ed.:, P. I. Dalko,), Wiley-VCH, Weinheim, 2007
25. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471
26. C. F. Barbas III, Angew. Chem. 2008, 120, 44
27. Angew. Chem. Int. Ed. 2008, 47, 42
28. A. M. Walji, D. W. C. MacMillan, Synlett 2007, 1477
29. D. W. C. MacMillan, Nature 2008, 455, 304
30. A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716
31. Angew. Chem. Int. Ed. 2008, 47, 4638
32. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232
33. Angew. Chem. Int. Ed. 2008, 47, 6138
34. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178.
35. A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204
36. Angew. Chem. Int. Ed. 2004, 43, 2152.
37. For a Lewis acid catalyzed aldol reaction of chloroacetaldehyde in the presence of water, see:, S. Kobayashi, I. Hachiya, J. Org. Chem. 1994, 59, 3590.
38. Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. 2006, 118, 972
39. Angew. Chem. Int. Ed. 2006, 45, 958
40. Y. Hayashi, S. Aratake, T. Okano, J. Takahashi, T. Sumiya, M. Shoji, Angew. Chem. 2006, 118, 5653
41. Angew. Chem. Int. Ed. 2006, 45, 5527
42. Y. Hayashi, Angew. Chem. 2006, 118, 8281
43. Angew. Chem. Int. Ed. 2006, 45, 8103
44. Y. Hayashi, S. Aratake, T. Itoh, T. Okano, T. Sumiya, M. Shoji, Chem. Commun. 2007, 957
45. S. Aratake, T. Itoh, T. Okano, T. Usui, M. Shoji, Y. Hayashi, Chem. Commun. 2007, 2524
46. S. Aratake, T. Itoh, T. Okano, N. Nagae, T. Sumiya, M. Shoji, Y. Hayashi, Chem. Eur. J. 2007, 13, 10246.
47. For selected reviews on organocatalyst-mediated reactions in the presence of water, see
48. J. Paradowska, M. Stodulski, J. Mlynarski, Angew. Chem. 2009, 121, 4352
49. Angew. Chem. Int. Ed. 2009, 48, 4288
50. M. Gruttadauria, F. Giacalone, R. Noto, Adv. Synth. Catal. 2009, 351, 33
51. M. Raj, V. K. Singh, Chem. Commun. 2009, 6687
52. N. Mase, C. F. Barbas III, Org. Biomol. Chem. 2010, 8, 4043.
53. M. Markert, U. Scheffler, R. Mahrwald, J. Am. Chem. Soc. 2009, 131, 16642.
54. Y. Hayashi, T. Itoh, S. Aratake, H. Ishikawa, Angew. Chem. 2008, 120, 2112
55. Angew. Chem. Int. Ed. 2008, 47, 2082
56. Y. Hayashi, S. Samanta, T. Itoh, H. Ishikawa, Org. Lett. 2008, 10, 5581
57. T. Urushima, Y. Yasui, H. Ishikawa, Y. Hayashi, Org. Lett. 2010, 12, 2966.
58. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284
59. Angew. Chem. Int. Ed. 2005, 44, 4212
60. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804
61. Angew. Chem. Int. Ed. 2005, 44, 794
62. M. Marigo, D. Fielenbach, A. Braunton, A. Kjasgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 804
63. Angew. Chem. Int. Ed. 2005, 44, 794. Review
64. C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042
65. Angew. Chem. Int. Ed. 2006, 45, 7876
66. A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922.
67. For the determination of the absolute configuration, see the Supporting Information.
68. A. Lattanzi, Org. Lett. 2005, 7, 2579
69. A. Russo, A. Lattanzi, Org. Biomol. Chem. 2010, 8, 2633.