Organocatalytic enantioselective aziridination of α,β- unsaturated aldehydes

Angewandte Chemie - International Edition

Volumn 46, Issue 5, 2007, Pages 778-781

  Vesely, Jan ^a   Ibrahem, Ismail ^a   Zhao, Gui Ling ^a   Rios, Ramon ^a   Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

amino acids; Asymmetric catalysis; Aziridines; Domino reactions; Organocatalysis

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; CATALYSIS; ESTERS;

Β-AMINO ACIDS; ASYMMETRIC CATALYSIS; AZIRIDINES; DOMINO REACTIONS; ORGANOCATALYSIS;

ALDEHYDES;

EID: 33846551705     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603810     Document Type: Article

References (80)

1. a) D. Tanner, Angew. Chem. 1994, 106, 625;
2. Angew. Chem. Int. Ed. 1994, 33, 599;
3. b) Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006;
4. c) E. N. Jacobsen in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 607;
5. d) J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247;
6. e) M. McCoull, F. A. Davis, Synthesis 2000, 1347.
7. See reference [1d]; a) Y. Na, S. Wang, H. Kohn, J. Am. Chem. Soc. 2002, 124, 4666;
8. for the biological properties of aziridines, see also: b) T. Burrage, E. Kramer, F. Brown, Vaccine 2000, 18, 2454;
9. c) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693;
10. d) S. Fürmeier, J. O. Metzger, Eur. J. Org. Chem. 2003, 649.
11. For a review, see: a) H. M. I. Osborn, J. Sweeney, Tetrahedron: Asymmetry 1997, 8, 1693;
12. see also: b) G. Righi, S. Pietrantonio, C. Bonini, Tetrahedron 2001, 57, 10 039;
13. c) D. Tanner, P. Somfai, Tetrahedron 1992, 48, 6069;
14. d) B. B. Lohray, Y. Gao, K. B. Sharpless, Tetrahedron Lett. 1989, 30, 2632.
15. P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905.
16. For selected examples see: a) D. A. Evans, M. M. Faul, M. T. Bilodeau, J. Org. Chem. 1991, 56, 6744;
17. b) D. A. Evans, M. M. Faul, M. T. Bilodeau, J. Am. Chem. Soc. 1994, 116, 2742;
18. c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Andersson, D. M. Barnes, J. Am. Chem. Soc. 1993, 115, 5328;
19. d) Z. Li, R. W. Quan, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5889;
20. e) R. W. Quan, Z. Li, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 8156;
21. f) K. B. Hansen, N. S. Finney, E. N. Jacobsen, Angew. Chem. 1995, 107, 750;
22. Angew. Chem. Int. Ed. Engl. 1995, 34, 676;
23. g) R. E. Lowenthal, S. Masamune, Tetrahedron Lett. 1991, 32, 7373;
24. h) K. Juhl, R. G. Hazell, K. A. Jørgensen, J. Chem. Soc. Perkin Trans. 1 1999, 2293;
25. i) J. M. Södergren, D. A. Alonso, P. G. Andersson, Tetrahedron: Asymmetry 1997, 8, 3563.
26. a) M. P. Doyle, B. J. Chapman, W. Hu, C. S. Peterson, M. A. McKervey, C. F. Garcia, Org. Lett. 1999, 1, 1327;
27. b) M. C. Pirrung, J. Zhang, Tetrahedron Lett. 1992, 33, 5987;
28. c) K. Guthikonda, J. DuBois, J. Am. Chem. Soc. 2002, 124, 13 672.
29. a) S.-M. Au, J.-S. Huang, W.-Y. Yu, W.-H. Fung, C.-M. Che, J. Am. Chem. Soc. 1999, 121, 9120;
30. b) J.-L. Liang, X.-Q. Yu, C.-M. Che, Chem. Commun. 2002, 124.
31. a) T. Katsuki, Synlett 2003, 281;
32. b) K. Noda, N. Hosoya, R. Irie, Y. Ito, T. Katsuki, Synlett 1993, 469;
33. c) J.-P. Simonato, J. Pécaut, R. Scheidt, J.-C. Marchon, Chem. Commun. 1999, 989;
34. d) A. K.-Y. Leung, J.-S. Huang, J.-L. Liang, C.-M. Che, Z.-Y. Zhou, Angew. Chem. 2003, 115, 354;
35. Angew. Chem. Int. Ed. 2003, 42, 340.
36. Y. Cui, C. He, J. Am. Chem. Soc. 2003, 125, 16 202.
37. a) J. C. Antilla, W. D. Wulff, J. Am. Chem. Soc. 1999, 121, 5099;
38. b) J. C. Antilla, W. D. Wulff, Angew. Chem. 2000, 112, 4692;
39. Angew. Chem. Int. Ed. 2000, 39, 4518.
40. a) V. K. Aggarwal, Synlett 1998, 329;
41. b) V. K. Aggarwal, A. Thompson, R. V. H. Jones, M. C. H. Standen, J. Org. Chem. 1996, 61, 8368;
42. c) V. K. Aggarwal, Angew. Chem. 2001, 113, 1482;
43. Angew. Chem. Int. Ed. 2001, 40, 1433.
44. For reviews, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840;
45. Angew. Chem. Int. Ed. 2001, 40, 3726;
46. b) B. List, Chem. Commun. 2006, 819;
47. c) R. O. Duthaler, Angew. Chem. 2003, 115, 1005;
48. Angew. Chem. Int. Ed. 2003, 42, 975;
49. d) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
50. Angew. Chem. Int. Ed. 2004, 43, 5138.
51. For selected examples, see: a) N. Halland, P. S. Aburell, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292;
52. Angew. Chem. Int. Ed. 2004, 43, 1272;
53. b) Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15 051;
54. c) J. W. Yang, M. T. Hechavarria Fonseca, B. List, J. Am. Chem. Soc. 2005, 127, 15 036;
55. d) M. Marigo, T. Schulte, J. Franzén, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15 710;
56. e) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962;
57. f) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Angew. Chem. 2003, 115, 4365;
58. Angew. Chem. Int. Ed. 2003, 42, 4233;
59. g) M. Marigo, J. Franzén, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964;
60. h). H. Sundén, I. Ibrahem, L. Eriksson, A. Córdova, Angew. Chem. 2005, 117, 4955;
61. Angew. Chem. Int. Ed. 2005, 44, 4877;
62. i) D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861;
63. j) H. Sundén, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2006, 47, 99;
64. k) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10 354.
65. For a summary of the concept of domino and tandem reactions, see: a) L. F. Tietze, Chem. Rev. 1996, 96, 115;
66. b) J. C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001.
67. a) I. Ibrahem, A. Córdova, Angew. Chem. 2006, 118, 1986;
68. Angew. Chem. Int. Ed. 2006, 45, 1952;
69. b) H. Sundén, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Chem. Eur. J., DOI: 10.1002/chem.200600572;
70. c) G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2006, 47, 7417.
71. For the imidazolidinone-catalyzed conjugate addition of silyloxycarbamates to enals, see: a) Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328;
72. b) for the reaction catalyzed by the chiral amine 9 between hydroxycarbamates and enals, see: I. Ibrahem, R. Rios, J. Vesely, G.-L. Zhao, A. Córdova, Chem. Commun., DOI: 10.1039/b613410f.
73. We also screened the reaction with nitrogen ylides as the nitrogen-atom-transfer agents, as they have been used in NaH-promoted aziridinations of α,β-unsaturated ketones; however, the desired reaction did not proceed; see: J. Xu, P. Jiao, J. Chem. Soc. Perkin Trans. 1 2002, 1491.
74. a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804;
75. Angew. Chem. Int. Ed. 2005, 44, 794;
76. b) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
77. Angew. Chem. Int. Ed. 2005, 44, 4212.
78. The 2-formylaziridines 3 are not particular stable and epimerize during column chromatography on silica gel. We also observed a slight decrease in the ee values at longer reaction times.
79. K. Y.-K. Chow, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 8126.
80. C. Cimarelli, G. Palmieri, J. Org. Chem. 1996, 61, 5557.