Addition reactions of iodomethyllithium to imines. A direct and efficient synthesis of aziridines and enantiopure amino aziridines

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4457-4460

  Concellón, José M ^a   Rodríguez Solla, Humberto ^a   Simal, Carmen ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349184526     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801607r     Document Type: Article

References (77)

1. (a) Wills, M. Contemp. Org. Synth. 1996, 3, 201.
2. (b) Coldham, I. Contemp. Org. Synth. 1997, 4, 136-163.
3. (c) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., McKillop, A., Eds.; Pergamon: Oxford, 1995; Vol 11, p 2.
4. For reviews on the synthesis and synthetic applications of functionalized organollithium compounds see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
5. (b) Nájera, C.; Yus, M. Recent Res. Dev. Org. Chem. 1997, 1, 67-96.
6. (c) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
7. (d) Yus, M.; Foubelo, F. Targets Heterocycl. Syst. 2002, 6, 136-171.
8. (e) Nájera, C.; Yus, M. Curr. Org. Chem. 2003, 7, 867-926.
9. (f) Chinchilla, R.; Nájera, C.; Yus, M. Tetrahedron 2005, 61, 3139-3176.
10. A synthesis of epoxides has been reported by reaction of iodomethyllithium with aldehydes and ketones at 0 °C: Concellon, J. M.; Cuervo, H.; Fernández-Fano, R. Tetrahedron 2001, 57, 8983-8987.
11. (a) Barluenga, J.; Fernández-Simón, J. L.; Concellón, J. M.; Yus, M. J. Chem. Soc., Chem. Commun. 1986, 1665-1665.
12. (b) Wallace, R. H.; Battle, W. Synth. Commun. 1995, 25, 127-133.
13. Reactions with aldehydes or ketones: (a) Barluenga, J.; Llavona, L.; Bernad, P. L.; Concellón, J. M. Tetrahedron Lett. 1993, 34, 3173-3176.
14. (b) Barluenga, J.; Baragana, B.; Concellón, J. M. J. Chem. Soc., Chem. Commun. 1994, 969-970.
15. (c) Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1999, 64, 2843-2846.
16. (d) Einhorn, C.; Allavena, C.; Luche, J. L. J. Chem. Soc., Chem. Commun. 1999, 333-334.
17. (e) Concellón, J. M.; Baragaña, B.; Riego, E. Tetrahedron Lett. 2000, 41, 4361-4362Reactions with esters:
18. (f) Barluenga, J.; Llavona, L.; Concellon, J. M.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1991, 297-300.
19. (g) Barluenga, J.; Llavona, L.; Yus, M.; Concellón, J. M. J. Chem. Soc., Perkin Trans. 1 1991, 2890-2890.
20. (h) Barluenga, J.; Baragana, B.; Concellon, J. M. J. Org. Chem. 1995, 60, 6696-6699.
21. (i) Concellón, J. M.; Bernad, P. L.; Riego, E.; García-Granda, S.; Forcén-Acebal, A. J. Org. Chem. 2001, 66, 2764-2768.
22. Reactions with carboxylic acid chlorides: (j) Barluenga, J.; Concellón, J. M.; Fernández-Simón, J. L.; Yus, M. J. Chem. Soc., Chem. Commun. 1988, 536-537.
23. (k) Barluenga, J.; Concellón, J. M.; Fernández- Simón, J. L.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1989, 77-80.
24. Reactions with boronic esters: (l) Matteson, D. S.; Sadhu, K. M. Tetrahedron Lett. 1986, 27, 795-798.
25. (m) Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819.
26. (n) Brown, H. C.; Gupta, A. K.; Rangaishenvi, M. V.; Prasad, J. V. N V. Heterocycles 1989, 28, 283-294.
27. (o) Brown, H. C.; Phadke, A. S.; Bhat, N. G. Tetrahedron Lett. 1993, 34, 7845-7848.
28. (p) Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8957-8960.
29. (q) Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8961-8964.
30. Reactions with N-protected 3-oxazolidin-5-ones: (r) Onishi, T.; Hirose, N.; Takashi, N.; Masakazu, N.; Kunisuke, I. Tetrahedron Lett. 2001, 42, 5883-5885.
31. To see synthetic application of aziridines: (a) Kasai, M.; Kono, M. Synlett 1992, 778-790.
32. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
33. (c) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon: Oxford, 1996; Vol 1A, pp 1-60.
34. (d) McCoull, W.; Davis, F. A. Synthesis 2000, 1347-1365.
35. (e) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247-258.
36. (f) Kumar, K. S. A.; Chaudhari, V. D.; Dhavale, D. D. Org. Biomol. Chem. 2008, 6, 703-711.
37. (g) Kumar, K. S. A.; Chaudhari, V. D.; Puranik, V. G.; Dhavale, D. D. Eur. J. Org. Chem. 2007, 489, 5-4901.
38. (h) Trost, B. M.; Dong, G. Org. Lett. 2007, 9, 2357-2359.
39. (i) Caldwell, J. J.; Craig, D. Angew. Chem., Int. Ed. 2007, 46, 2631-2634.
40. (j) Crawley, S. L.; Funk, R. L. Org. Lett. 2006, 8, 3995-3998.
41. (k) Banwell, M. G.; Lupton, D. W. Org. Biomol. Chem. 2005, 3, 213-215.
42. (l) Smith, A. B., III; Kim, D. Org. Lett. 2004, 6, 1493-1495.
43. (a) Gerhart, F.; Higgins, W.; Tardif, C.; Ducep, J. J. Med. Chem. 1990, 33, 2157-2162.
44. (b) Lefemine, D. V.; Dann, M.; Barbatschi, F.; Hausmann, W. K.; Zbinovsky, V.; Monnikendam, P.; Adam, J.; Bohonos, N. J. Am. Chem. Soc. 1962, 84, 3184-3185.
45. (c) Hau, I.; Kohn, H. J. Org. Chem. 1991, 56, 4648-4653.
46. (d) Skibo, E. B.; Islam, I.; Heileman, M. J.; Schultz, W. G. J. Med. Chem. 1994, 37, 78-92.
47. (a) Davis, F. A.; Zhou, P.; Liang, C. -H.; Reddy, R. E. Tetrahedron: Asymmetry 1995, 6, 1511-1514.
48. (b) García-Ruano, J. L.; Fernandez, I.; del Prado-Catalina, M.; Alcudia-Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414.
49. (c) Higashiyma, K.; Matsumura, M.; Shiogama, A.; Yamauchi, T.; Ohmiya, S. Heterocycles 2002, 58, 85-88.
50. (d) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 1353-1354.
51. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Synlett 2003, 1985-1988.
52. (f) Miduka, W. H. Tetrahedron Lett. 2007, 48, 3907-3910.
53. (g) Aggarwal, V. K.; Stenson, R. A.; Jones, R. V. H.; Fieldhouse, R.; Blacker, J. Tetrahedron Lett. 2001, 42, 1587-1589.
54. tom Dieck, H.; Haupt, E. Chem. Ber. 1983, 116, 1540-1546.
55. (a) Singh, G. S.; D'hooghe, M.; De Kimpe, N. Chem. Rev. 2007, 107, 2080-2135.
56. (b) De Kimpe, N.; Verhé, R.; De Buyck, L.; Schamp, N. Synth. Commun. 1975, 5, 269-274.
57. (c) De Kimpe, N.; Schamp, N.; Verhé, R. Synth. Commun. 1975, 5, 403-408.
58. (d) De Kimpe, N.; Verhé. R.; De Buyck, L.; Schamp, N. J. Org. Chem. 1980, 45, 5319-5325.
59. (e) De Kimpe, N.; Sulmon, P.; Verhé, R.; De Buyek, L.; Schamp, N. J. Org. Chem. 1983, 48, 4320-4326.
60. (f) De Kimpe, N.; Moens, L. Tetrahedron 1990, 46, 2965-2974.
61. (g) Denolf, B.; Mangelinekx, S.; Törnroos, K. W.; De Kimpe, N. Org. Lett. 2006, 8, 3129-3132.
62. (h) Denolf, B.; Leemans, E.; De Kimpe, N. J. Org. Chem. 2007, 72, 3211-3217.
63. Savoia, D.; Alvaro, G.; Di Fabio, R.; Gualandi, A.; Fiorelli, C. J. Org. Chem. 2006, 71, 9373-9381.
64. Reetz, M. T.; Lee, W. K. Org. Lett. 2001, 3, 3119-3120.
65. Wang, Y.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156-8157.
66. Alonso, D. A.; Andersson, P. G. J. Org. Chem. 1998, 63, 9455-9461.
67. (a) Previously, we reported the synthesis of nonactivated enantiopure syn-aminoalkyl aziridines by reduction of α-amino ketimines derived from 1-aminoalkyl chloromethyl ketones.
68. See ref 5i. (b) Reetz et al reported the synthesis of nonactivated enantiopure anti-aminoalkyl aziridines. See ref 12.
69. (a) Concellón, J. M.; Riego, E. J. Org. Chem. 2003, 68, 6407-6410.
70. (b) Concellón, J. M.; Riego, E.; Álvarez. J. R. J. Org. Chem. 2003, 68, 9242-9246.
71. (c) Concellón, J. M.; Álvarez, J. R.; García-Granda, S.; Díaz, M. R. Angew. Chem., Int. Ed. 2004, 43, 4333-4336.
72. (d) Concellón, J. M.; Riego, E.; Rivero, I. A.; Ochoa, A. J. Org. Chem. 2004, 69, 6244-6248.
73. (e) Concellón, J. M.; Riego, E.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Org. Lett. 2004, 6, 4499-4501.
74. (f) Concellón; J. M.; Bernad, P. L.; Suárez, J. R. Chem.-Eur. J. 2005, 11, 4492-4501.
75. (g) Concellón, J. M.; Bernad, P. L.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. J. Org. Chem. 2005, 70, 9411-9416.
76. Sisko, J.; Weinreb, S. M. J. Org. Chem. 1990, 55, 393-395.
77. An excess of iodomethyllithium was necessary due to the presence of N-tosylamine in the mixture reaction, as a consequence of the N-sulfinyl-p-toluenesulfonamide required for the synthesis of aldimines 6, which is purchased from TCI with a purity ∼70%.