An amine-promoted aziridination of chalcones

Angewandte Chemie - International Edition

Volumn 45, Issue 47, 2006, Pages 8005-8008

  Shen, Yu Mei ^a   Zhao, Mei Xin ^a   Xu, Jiaxi ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

Asymmetric catalysis; Aziridines; Chalcones; Nitrogen heterocycles; Small ring systems

Indexed keywords

AMINES; CATALYSIS; NITROGEN COMPOUNDS; REACTION KINETICS;

ASYMMETRIC CATALYSIS; AZIRIDINES; CHALCONES; NITROGEN HETEROCYCLES; SMALL RING SYSTEMS;

KETONES;

AMINE; AZIRIDINE DERIVATIVE; CHALCONE DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY;

AMINES; AZIRIDINES; CATALYSIS; CHALCONES; HETEROCYCLIC COMPOUNDS; MODELS, CHEMICAL; NITROGEN;

EID: 33845500079     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602586     Document Type: Article

References (97)

1. For leading reviews on the synthesis and application of aziridines, see: a) D. Tanner, Angew. Chem. 1994, 106, 625;
2. Angew. Chem. Int. Ed. Engl. 1994, 33, 599;
3. b) J. Du Bois, C. S. Tomooka, J. Hong, E. M. Carreira, Acc. Chem. Res. 1997, 30, 364;
4. c) A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341;
5. d) H. M. I. Osborn, J. Sweeney, Tetrahedron: Asymmetry 1997, 8, 1693;
6. e) T. Ibuka, Chem. Soc. Rev. 1998, 27, 145;
7. f) E. N. Jacobsen in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, chap. 17;
8. g) R. S. Atkinson, Tetrahedron 1999, 55, 1519;
9. h) W. McCoull, F. A. Davis, Synthesis 2000, 1347;
10. i) J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247;
11. j) M. D. Redlich, M. F. Mayer, M. M. Hossain, Aldrichimica Acta 2003, 36, 3;
12. k) P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905;
13. l) X. E. Hu, Tetrahedron 2004, 60, 2701;
14. m) Y. Tang, S. Ye, X.-L. Sun, Synlett 2005, 2720;
15. n) T. Katsuki, Chem. Lett. 2005, 34, 1304;
16. o) I. D. G. Watson, L. Yu, A. K. Yudin, Acc. Chem. Res. 2006, 39, 194.
17. For leading references on the bromine- and iodine-catalyzed aziridination of olefins, see: a) J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 6844;
18. b) T. Ando, D. Kano, S. Minakata, I. Ryu, M. Komatsu, Tetrahedron 1998, 54, 13485.
19. For leading references on the asymmetric aza-Darzens-type aziridination, see: a) F. A. Davis, P. Zhou, G. V. Reddy, J. Org. Chem. 1994, 59, 3243;
20. b) A. B. McLaren, J. B. Sweeney, Org. Lett. 1999, 1, 1339;
21. c) S. Hanessian, L.-D. Cantin, Tetrahedron Lett 2000, 41, 787;
22. d) T. Satoh, Y. Fukuda, Tetrahedron 2003, 59, 9803;
23. e) F. Ferreira, M. Audouin, F. Chemla, Chem. Eur. J. 2005, 11, 5269.
24. For leading references on the aziridination of imines with ylides, see: a) A.-H. Li, L.-X. Dai, X.-L. Hou, Chem. Commun. 1996, 491;
25. b) V. K. Aggarwal, A. Thompson, R. V. H. Jones, M. C. H. Standen, J. Org. Chem. 1996, 61, 8368;
26. c) A.-H. Li, Y.-G. Zhou, L.-X. Dai, X.-L. Hou, L.-J. Xia, L. Lin, Angew. Chem. 1997, 109, 1375;
27. Angew. Chem. Int. Ed. Engl. 1997, 36, 1317;
28. d) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482;
29. Angew. Chem. Int. Ed. 2001, 40, 1433.
30. For leading references on the aziridination of imines with diazo compounds, see: a) R. Bartnik, G. Mloston, Synthesis 1983, 924;
31. b) K. B. Hansen, N. S. Finney, E. N. Jacobsen, Angew. Chem. 1995, 107, 750;
32. Angew. Chem. Int. Ed. Engl. 1995, 34, 676;
33. c) J. C. Antilla, W. D. Wulff, J. Am. Chem. Soc. 1999, 121, 5099;
34. d) K. Juhl, R. G. Hazell, K. A. Jørgensen, J. Chem. Soc. Perkin Trans. 1 1999, 2293;
35. e) V. K. Aggarwal, M. Ferrara, Org. Lett. 2000, 2, 4107.
36. For leading references on the metal-catalyzed aziridination of olefins, see: for racemic systems: a) H. Kwart, A. A. Khan, J. Am. Chem. Soc. 1967, 89, 1951;
37. b) J. T. Groves, T. Takahashi, J. Am. Chem. Soc. 1983, 105, 2073;
38. c) D. Mansuy, J.-P. Mahy, A. Dureault, G. Bedi, P. Battioni, J. Chem. Soc. Chem. Commun. 1984, 1161;
39. d) D. A. Evans, M. M. Faul, M. T. Bilodeau, J. Org. Chem. 1991, 56, 6744;
40. e) D. A. Evans, M. M. Faul, M. T. Bilodeau, J. Am. Chem. Soc. 1994, 116, 2742;
41. f) J. Du Bois, J. Hong, E. M. Carreira, M. W. Day, J. Am. Chem. Soc. 1996, 118, 915;
42. g) S.-M. Au, J.-S. Huang, W.-Y. Yu, W.-H. Fung, C.-M. Che, J. Am. Chem. Soc. 1999, 121, 9120;
43. h) P. Brandt, M. J. Södergren, P. G. Andersson, P.-O. Norrby, J. Am. Chem. Soc. 2000, 122, 8013;
44. i) P. Dauban, L. Sanière, A. Tarrade, R. H. Dodd, J. Am. Chem. Soc. 2001, 123, 7707;
45. j) A. Padwa, T. Stengel, Org. Lett. 2002, 4, 2137;
46. k) K. Guthikonda, J. Du Bois, J. Am. Chem. Soc. 2002, 124, 13 672;
47. l) Y. Cui, C. He, J. Am. Chem. Soc. 2003, 125, 16202;
48. m) W.-L. Man, W. W. Y. Lam, S.-M. Yiu, T.-C. Lau, S.-M. Peng, J. Am. Chem. Soc. 2004, 126, 15 336;
49. n) A. J. Catino, J. M. Nichols, R. E. Forslund, M. P. Doyle, Org. Lett. 2005, 7, 2787;
50. o) H. Lebel, K. Huard, S. Lectard, J. Am. Chem. Soc. 2005, 127, 14 198.
51. for asymmetric systems: p) D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726;
52. q) R. E. Lowenthal, S. Masamune, Tetrahedron Lett. 1991, 32, 7373;
53. r) Z. Li, K. R. Conser, E. N. Jacobsen, J. Am. Chem. Soc. 1993, 115, 5326;
54. s) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, D. M. Barnes, J. Am. Chem. Soc. 1993, 115, 5328;
55. t) Z. Li, R. W. Quan, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5889;
56. u) S. Minakata, T. Ando, M. Nishimura, I. Ryu, M. Komatsu, Angew. Chem. 1998, 110, 3596;
57. Angew. Chem. Int. Ed. 1998, 37, 3392;
58. v) C. J. Sanders, K. M. Gillespie, D. Bell, P. Scott, J. Am. Chem. Soc. 2000, 122, 7132;
59. w) H. Kawabata, K. Omura, T. Katsuki, Tetrahedron Lett. 2006, 47, 1571.
60. For recent leading references on nitrogen transfer to olefins using N-acetoxyamino compounds, see: a) R. S. Atkinson, R. D. Draycott, D. J. Hirst, M. J. Parratt, T. M. Raynham, Tetrahedron Lett. 2002, 43, 2083;
61. b) T. Siu, A. K. Yudin, J. Am. Chem. Soc. 2002, 124, 530;
62. c) K.-S. Yang, K. Chen, Org. Lett. 2002, 4, 1107;
63. d) J. Li, P. W. H. Chan, C.-M. Che, Org. Lett. 2005, 7, 5801.
64. For leading references on the addition of primary amines to 2-halo-substituted α,β-unsaturated carbonylcompounds, see: a) O. Ploux, M. Caruso, G. Chassaing, A. Marquet, J. Org. Chem. 1988, 53, 3154;
65. b) P. Garner, O. Dogan, S. Pillai, Tetrahedron Lett. 1994, 35,1653;
66. c) G. Cardillo, L. Gentilucci, C Tomasini, M. P. V. Castejon-Bordas, Tetrahedron: Asymmetry 1996, 7, 755;
67. d) M. T. Barros, C. D. Maycock, M. R. Ventura, Tetrahedron Lett. 2002, 43, 4329;
68. e) A. Mekonnen, R. Carlson, Tetrahedron 2006, 62, 852.
69. For leading references using RONH2, see: a) I. Coldham, A. J. Collis, R. J. Mould, R. E. Rathmell, Tetrahedron Lett. 1995, 36, 3557;
70. b) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, Angew. Chem. 1996, 108, 1939;
71. Angew. Chem. Int. Ed. Engl. 1996, 35, 1848;
72. c) X. L. Jin, H. Sugihara, K. Daikai, H. Tateishi, Y. Z. Jin, H. Furuno, J. Inanaga, Tetrahedron 2002, 58, 8321;
73. d) N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 16 178.
74. 2R, see: a) S. Fioravanti, L. Pellacani, S. Stabile, P. A. Tardella, R. Ballini, Tetrahedron 1998, 54, 6269;
75. b) S. Fioravanti, A. Morreale, L. Pellacani, P. A. Tardella, J. Org. Chem. 2002, 67, 4972;
76. c) D. Colantoni, S. Fioravanti, L. Pellacani, P. A. Tardella, Org. Lett. 2004, 6, 197.
77. 2S=NH, see: a) T. Yoshimura, T. Akasaka, N. Furukawa, S. Oae, Heterocycles 1977, 7, 287;
78. b) N. Furukawa, T. Yoshimura, M. Ohtsu, T. Akasaka, S. Oae, Tetrahedron 1980, 36, 73.
79. For leading references using diaziridine, see: a) K. Hori, H. Sugihara, Y. N. Ito, T. Katsuki, Tetrahedron Lett. 1999, 40, 5207;
80. b) H. Ishihara, Y. N. Ito, T. Katsuki, Chem. Lett. 2001, 984;
81. c) H. Ishihara, K. Hori, H. Sugihara, Y. N. Ito, T. Katsuki, Helv. Chim. Acta 2002, 85, 4272.
82. For a recent leading reference on the aziridination by addition of azides to olefins, see: J. M. Mahoney, C. R. Smith, J. N. Johnston, J. Am. Chem. Soc. 2005, 127, 1354.
83. 3 or trimethyl-silyltriflate, see: a) V. F. Rudchenko, S. M. Ignatov, R. G. Kostyanovsky, J. Chem. Soc. Chem. Commun. 1990, 261;
84. b) E. Vedejs, H. Sano, Tetrahedron Lett. 1992, 33, 3261.
85. For aziridination of olefins with MSH, see: a) J. C. Bottaro, J. Chem. Soc. Chem. Commun. 1980, 560;
86. b) P. Métra, J. Hamelin, J. Chem. Soc. Chem. Commun. 1980, 1038.
87. I. Ikeda, Y. Machii, M. Okahara, Synthesis 1980, 650.
88. G. A. Olah, M. B. Sassaman, M. Zuanic, C. B. Rao, G. K. S. Prakash, J. Org. Chem. 1992, 57, 1585.
89. a) J. Xu, P. Jiao, J. Chem. Soc. Perkin Trans. 1 2002, 1491;
90. Erratum: b) J. Xu, P. Jiao, J. Chem. Soc. Perkin Trans. 1 2002, 2561.
91. For leading references on amination of tertiary amines with MSH, see: a) Y. Tamura, J. Minamikawa, Y. Kita, J. H. Kim, M. Ikeda, Tetrahedron 1973, 29, 1063 ;
92. b) Y. Tamura, J. Minamikawa, M. Ikeda, Synthesis 1977, 1.
93. For the preparation of MSH, see: a) C. R. Johnson, R. A. Kirchhoff, H. G. Corkins, J. Org. Chem. 1974, 39, 2458;
94. b) Y. Tamura, J. Minamikawa, K. Sumoto, S. Fujii, M. Ikeda, J. Org. Chem. 1973, 38, 1239.
95. For an amine-catalyzed asymmetric cyclopropanation, see: C. D. Papageorgiou, M. A. Cubillo de Dios, S. V. Ley, M. J. Gaunt, Angew. Chem. 2004,116, 4741;
96. Angew. Chem. Int. Ed. 2004, 43, 4641.
97. About 93 % of the chiral Tröger's base could be recovered after the reaction, and the recovered chiral amine provided similar reactivity and enantioselectivity for the aziridination.