Aziridination of aliphatic alkenes catalyzed by N-heterocyclic carbene copper complexes

Organic Letters

Volumn 10, Issue 7, 2008, Pages 1497-1500

  Xu, Qun ^a   Appella, Daniel H ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; CARBENE; COPPER; DRUG DERIVATIVE; METHANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKENES; AZIRIDINES; CATALYSIS; COPPER; METHANE; MOLECULAR STRUCTURE;

EID: 45849138214     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800288b     Document Type: Article

References (94)

1. (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
2. (b) Zwanenburg, B.; ten Holte, P. Top. Curr. Chem. 2001, 216, 93.
3. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
4. (d) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
5. Reviews: (a) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
6. (b) Dauban, P.; Dodd, R. H. Synlett 2003, 1571.
7. (c) Espino, C. G.; Du Bois J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; Chapter 17, pp 379-416.
8. (d) Hafen, J. A. Curr. Org. Chem. 2005, 9, 657.
9. (e) Watson, I. D. G.; Yu, L.; Yudin, A. K. Acc. Chem. Res. 2006, 39, 194.
10. (f) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618.
11. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
12. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744.
13. Application in total synthesis: (a) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752.
14. (b) Masse, C. E.; Knight, B. S.; Stavropoulos, P.; Panek, J. S. J. Am. Chem. Soc. 1997, 119, 6040.
15. (c) Overman, L. E.; Tomasi, A. L. J. Am. Chem. Soc. 1998, 120, 4039.
16. (d) Sudau, A.; Münch, W.; Bats, J. W.; Nubbemeyer, U. Chem. - Eur. J. 2001, 7, 611.
17. (e) White, R. D.; Wood, J. L. Org. Lett. 2001, 3, 1825.
18. (f) Ahmadian, M.; Khare, N. K.; Riordan, J. M.; Klon, A. E.; Borhani, D. W. Tetrahedron 2001, 57, 9899.
19. (g) Baron, E.; O'Brien, P.; Towers, T. D. Tetrahedron Lett. 2002, 43, 723.
20. (h) Di Chenna, P. H.; Dauban, P.; Ghini, A.; Baggio, R.; Garland, M. T.; Burton, G.; Dodd, R. H. Tetrahedron 2003, 59, 1009.
21. (i) White, R. D.; Keaney, G. F.; Slown, C. D.; Wood, J. L. Org. Lett. 2004, 6, 1123.
22. (j) Provoost, O. Y.; Hedley, S. J.; Hazelwood, A. J.; Harrity, J. P. A. Tetrahedron Lett. 2006, 47, 331.
23. (k) Kessler, A.; Faure, H.; Petrel, C.; Rognan, D,; Césario, M.; Ruat, M.; Dauban, P.; Dodd, R. H. J. Med. Chem. 2006, 49, 5119.
24. (a) Dauban, P.; Saniere, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
25. (b) Kwong, H.-L.; Liu, D.; Chan, K.-Y.; Lee, C.-S.; Huang, K.-H.; Che, C.-M. Tetrahedron Lett. 2004, 45, 3965.
26. (a) Li, Z.; Conser, K.; Jacobson, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
27. (b) Knight, J. G.; Muldowney, M. D. Synlett 1995, 949.
28. (c) Brookhart, M.; DiazRequejo, M. M.; Perez, P. J.; Templeton, J. L. Organometallics 1997, 16, 4399.
29. (d) Södergren, M. J.; Alonso, D. A.; Bedekar, A.; Andersson, P. G. Tetrahedron Lett. 1997, 38, 6897.
30. (e) Halfen, J. A.; Hallman, J. K.; Schultz, J. A.; Emerson, J. P. Organometallics 1999, 18, 5435.
31. (f) Dauban, P.; Dodd, R. H. J. Org. Chem. 1999, 64, 5304.
32. (g) Brandt, P.; Sodergren, M. J.; Andersson, P. G.; Norrby, P. O. J. Am. Chem. Soc. 2000, 122, 8013.
33. (h) Sanders, C. J.; Gillespie, K. M.; Bell, D.; Scott, P. J. Am. Chem. Soc. 2000, 122, 7132.
34. (i) Handy, S. T.; Czopp, M. Org. Lett. 2001, 3, 1423.
35. (j) Halfen, J. A.; Fox, D. C.; Mehn, M. P.; Que, L., Jr. Inorg. Chem. 2001, 40, 5060.
36. (k) Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481.
37. (l) Gillespie, K. M.; Sanders, C. J.; OrShaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450.
38. (m) Vedernikov, A. N.; Caulton, K. G. Org. Lett. 2003, 5, 2591.
39. (n) Di Chenna, P. H.; Robert-Peillard, F.; Dauban, P.; Dodd, R. H. Org. Lett. 2004, 6, 4503.
40. (o) Leca, D.; Toussaint, A.; Mareau, C.; Fensterbank, L.; Lacote, E.; Malacria, M. Org. Lett. 2004, 6, 3573.
41. (p) Han, H.; Bae, I.; Yoo, E. J.; Lee, J.; Do, Y.; Chang, S. Org. Lett. 2004, 6, 4109.
42. (q) Mairena, M. A.; Diaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. Organometallics 2004, 23, 253.
43. (r) Mohr, F.; Binfield, S. A.; Fettinger, J. C.; Vedernikov, A. N. J. Org. Chem. 2005, 70, 4833.
44. (s) Sun, W.; Herdtweck, E.; Kuhn, F. E. New J. Chem. 2005, 29, 1577.
45. (t) Lebel, H.; Lectard, S.; Parmentier, M. Org. Lett. 2007, 9, 4797.
46. (a) Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 105, 6728.
47. (b) Müller, P.; Baud, C.; Jacquier, Y. Can. J. Chem. 1998, 76, 738.
48. (c) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672.
49. (d) Levites-Agababa, E.; Menhaji, E.; Perlson, L. N.; Rojas, C. M. Org. Lett. 2002, 4, 863.
50. (e) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137.
51. (f) Liang, J.-L.; Yuan, S.-X.; Chan, P.-W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507.
52. (g) Padwa, A.; Flick, A. C.; Leverett, C. A.; Stengel, T. J. Org. Chem. 2004, 69, 6377.
53. (h) Fruit, C. Robert-Peillard, F.; Bernardinelli, G.; Müller, P.; Dodd, R. H.; Dauban, P. Tetrahedron: Asymmetry 2005, 16, 3484.
54. (i) Guthikonda, K.; Wehn, P. M.; Caliando, B. J.; Du Bois, J. Tetrahedron 2006, 62, 11331.
55. (a) S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C.-M. J. Am. Chem. Soc. 1999, 121, 9120.
56. (b) Liang, J.-L.; Huang, J. S.; Yu, X. Q.; Zhu, N. Y.; Che, C.-M. Chem. - Eur. J. 2002, 8, 1563.
57. (c) Omura, K.; Murakami, M.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Lett. 2003, 32, 254.
58. (d) Liang, J.-L.; Yuan, S.-X.; Huang, J. S.; Che, C.-M. J. Org. Chem. 2004, 69, 3610.
59. (e) Kawabata, H.; Omura, K.; Katsuki, T. Tetrahedron Lett. 2006, 47, 1571.
60. (f) Piangioline, C.; Gallo, E.; Caselli, A.; Fantauzzi, S.; Ragaini, F.; Cenini, S. Eur. J. Org. Chem. 2007, 743.
61. (a) Groves, J. T.; Takahashi, T. J. Am. Soc. Chem. 1983, 105, 2073.
62. (b) Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469.
63. (c) Nishikori, H.; Katsuki, T. Tetrahedron Lett. 1996, 37, 9245.
64. (d) Nishimura, M.; Minakata, S.; Thongchant, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 2000, 41, 7089.
65. Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
66. Li, Z.; Ding, X.; He, C. J. Org. Chem. 2006, 71, 5876.
67. (a) Mahy, J. P.; Battioni, P.; Mansuy, D. J. Am. Soc. Chem. 1986, 108, 1079.
68. (b) Heuss, B. D.; Mayer, M. F.; Dennis, S.; Hossain, M. M. Inorg. Chim. Acta 2003, 342, 301.
69. (c) Vyas, R.; Gao, G.-Y.; Harden, J. D.; Zhang, X. P. Org. Lett. 2004, 6, 1907.
70. (a) Gao, G.-Y.; Harden, J. D.; Zhang, X. P. Org. Lett. 2005, 7, 3191.
71. (b) Gao, G. Y.; Jones, J. E.; Vyas, R.; Handen, J, D.; Zhang, X. P. J. Org. Chem. 2006, 71, 6655.
72. Xu, Q.; Appella, D. H. J. Org. Chem. 2006, 71, 8655.
73. Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530.
74. For reviews, see: (a) Arduengo, A. J. Acc. Chem. Res. 1999, 32, 913.
75. (b) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
76. (c) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
77. (d) Carbene Chemistry. From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Dekker: New York, 2002.
78. (e) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
79. (f) Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239.
80. (g) Scott, N. M.; Nolan, S. P. Eur. J. Inorg. Chem. 2005, 1815.
81. (h) Hahn, F. E. Angew. Chem., Int. Ed. 2006, 45, 1348.
82. (i) N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
83. (j) N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry, Vol 21; Springer: Berlin, 2007.
84. (a) Arnold, P. L.; Rodden, M.; Davis, K. M.; Scarisbrick, A. C.; Blake, A. J.; Wilson, C. Chem. Commun. 2004, 1612.
85. (b) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889.
86. For a recent review on NHC-copper complexes in homogeneous catalysis, see: (a) Deíz-González, S., Nolan, S. P. Synlett 2007, 14, 2158.
87. Cyclopropanation: (b) Fructos, M. R.; Belderrain, T. R.; Nicasio, M. C.; Nolan, S. P.; Kaur, H.; Díaz-Requejo, M. M.; Pérez, P. J. J. Am. Chem. Soc. 2004, 126, 10846.
88. (c) Gawley, R. E.; Narayan, S. Chem. Commun. 2005, 5109.
89. (a) Trost, B. M. Dong, G. J. Am. Chem. Soc. 2006, 128, 6054.
90. (b) Liu, R. Herron, S, R. Fleming. S. A. J. Org. Chem. 2007, 72, 5587.
91. Welle, A. Deíz-González, S. Tinant, B. Nolan, S. P. Riant, O. Org. Lett. 2006, 8, 6059.
92. Portionwise addition of oxidant usually has a beneficial effect in aziridination and amidation reactions involving nitrenes, see: ref 5a, and Fioiri, K. W.; Du Bois, J. J. Am. Soc. Chem. 2007, 129, 562.
93. Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425.
94. Masuno, M. N.; Young, D. M.; Hoepker, A. C.; Skepper, C. K.; Molinski, T. F. J. Org. Chem. 2005, 70, 4162.