One-pot synthesis of β-amino/β-hydroxy selenides and sulfides from aziridines and epoxides

Synthesis

Volumn , Issue 19, 2009, Pages 3267-3278

  Ganesh, Venkataraman ^a   Chandrasekaran, Srinivasan ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

amino selenide; amino sulfide; hydroxy selenide; hydroxy sulfide; Aziridine; Epoxide; Rongalite

Indexed keywords

AZIRIDINE; AZIRIDINES; DISELENIDES; EPOXIDE; IN-SITU; ONE POT; ONE-POT SYNTHESIS; REGIO-SELECTIVE; RING OPENING; RONGALITE; SELENIDES; THIOLATES;

AMINES; IONIC LIQUIDS; SELENIUM COMPOUNDS; SODIUM;

AMINATION;

AZIRIDINE DERIVATIVE; EPOXIDE; HYDROXYAMINO ACID; SELENIDE; SULFIDE;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING;

EID: 70449337395     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216960     Document Type: Article

References (72)

1. For reviews on this topic, Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G. Tetrahedron 1997, 53, 12789.
2. Chakraborty, T. K.; Ghosh, S.; Jayaprakash, S. Curr. Med. Chem. 2002, 9, 421.
3. Moroder, R. J. J. Pept. Sci. 2005, 11, 187.
4. Pegoraro, S.; Fiori, S.; Cramer, J.; Rudolph-Böhner, S.; Moroder, L. Protein Sci. 1999, 8, 1605.
5. Fiori, S.; Pegoraro, S.; Rudolph-Böhner, S.; Cramer, J.; Moroder, L. Biopolymers 2000, 53, 550.
6. Mugesh, G.; du Mont, W. W.; Sies, H. Chem. Rev. 2001, 101, 2125.
7. Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2003, 125, 13455.
8. Nogueria, C. W.; Zeni, G.; Roch, J. B. T. Chem. Rev. 2004, 104, 6255.
9. Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851.
10. Ku, T. W.; Kondrad, K. H.; Gleason, J. G. J. Org. Chem. 1989, 54, 3487.
11. Kolb, H. C.; Sharpless, K. B. Tetrahedron 1992, 48, 10515.
12. Rinehart, K. L. Med. Res. Rev. 2000, 20, 1.
13. Kang, J.; Lee, J. W.; Kim, J. I. J. Chem. Soc., Chem. Commun. 1994, 2009.
14. Hof, R. P.; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. M. Tetrahedron: Asymmetry 1994, 5, 31.
15. Jin, M. J.; Ahn, S. J.; Lee, K. S. Tetrahedron Lett. 37, 8767.
16. Christoffers, J. Liebigs Ann./Recl. 1997, 1353.
17. Fulton, D. A.; Gibson, C. L. Tetrahedron Lett. 38, 2019.
18. Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353.
19. Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010.
20. Jimeno, C.; Moyano, A.; Pericàs, M. A.; Riera, A. Synlett 2001, 1155.
21. Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagn, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
22. Paolis, M. D.; Blankenstein, J.; Bois-Choussy, M.; Zhu, J. Org. Lett. 2002, 4, 1235.
23. Trost, B. M.; Ochiai, M.; McDougal, P. G. J. Am. Chem. Soc. 1978, 100, 7103.
24. Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. J. Org. Chem. 2003, 68, 8248; and references therein.
25. Lindley, J. Tetrahedron Lett. 1984, 25, 1433.
26. Yunoki, S. I.; Takimiya, K.; Aso, Y.; Otsubo, T. Tetrahedron Lett. 1997, 38, 3017.
27. Yin, J.; Pidgeon, C. Tetrahedron Lett. 1997, 38, 5953.
28. Shah, S. T. A.; Khan, K. M.; Heinrich, A. M.; Voelter, W. Tetrahedron Lett. 2002, 43, 8281.
29. Herriott, A. W.; Picker, D. Synthesis 1975, 447.
30. Degani, I.; Fochi, R.; Regondi, V. Synthesis 1983, 630.
31. Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099.
32. Page, P. C. B.; Klair, S. S.; Brown, M. P.; Harding, M. M.; Smith, C. S.; Maginn, S. J.; Mulley, S. Tetrahedron Lett. 1988, 29, 4477.
33. Li, C. J.; Harpp, D. N. Tetrahedron Lett. 1992, 33, 7293.
34. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
35. Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
36. Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
37. Andreadou, I.; Menge, W. M. P. B.; Commandeur, J. N. M.; Worthington, E. A.; Vermeulen, N. P. E. J. Med. Chem. 1996, 39, 2040.
38. Sakakibara, M.; Katsumata, K.; Watanabe, Y.; Toru, T.; Ueno, Y. Synthesis 1992, 377.
39. Bhasin, K. K.; Singh, N.; Kumar, R.; Deepali, D. G.; Mehta, S. K.; Klapoetke, T. M.; Crawford, M. J. J. Organomet. Chem. 2004, 689, 3327.
40. Crich, D.; Grant, D. J. Org. Chem. 2005, 68, 7921.
41. Ranu, B. C.; Mandal, T.; Samanta, S. Org. Lett. 2003, 5, 1439.
42. Ranu, B. C.; Mandal, T. J. Org. Chem. 2004, 69, 5793.
43. Braga, A. L.; Schneider, P. H.; Paixão, M. W.; Deobald, A. M.; Peppe, C.; Bottega, D. J. Org. Chem. 2006, 71, 4305.
44. Munbunjong, W.; Lee, E. H.; Ngernmaneerat, P.; Kim, S. J.; Singh, G.; Chavasiri, W.; Jang, D. O. Tetrahedron 2009, 65, 2467.
45. Braga, A. L.; Lüdtke, D. S.; Paixão, M. W.; Alberto, E. E.; Stefani, H. A.; Juliano, L. Eur. J. Org. Chem. 2005, 4260.
46. Tiecco, M.; Testaferri, L.; Bagnoli, L.; Scarponi, C.; Temperini, A.; Marini, F.; Santi, C. Tetrahedron: Asymmetry 2007, 18, 2758.
47. Wu, J.; Sun, X.; Li, Y. Eur. J. Org. Chem. 2005, 20, 4271.
48. Zhang, W. X.; Ye, K.; Ruan, S.; Chen, Z. X.; Xia, Q. H. Chin. J. Chem. 2007, 25, 1758.
49. Sureshkumar, D.; Gunasundari, T.; Ganesh, V.; Chandrasekaran, S. J. Org. Chem. 2007, 72, 2106.
50. Devan, N.; Sridhar, P. R.; Prabhu, K. R.; Chandrasekaran, S. J. Org. Chem. 2002, 67, 9417.
51. Wakselman, C.; Tordeux, M.; Clavel, J. L.; Langlois, B. J. Chem. Soc., Chem. Commun. 1991, 993.
52. Clavel, J. L.; Langlois, B.; Nantermet, R.; Tordeux, M.; Wakselman, C. J. Chem. Soc., Perkin Trans. 1 1992, 3371.
53. Tercio, J.; Ferreira, B.; Comasseto, J. V. Synth. Commun. 1986, 1335.
54. Tang, R. Y.; Zhong, P.; Lin, Q. L. J. Fluorine Chem. 2006, 127, 948.
55. Tang, R. Y.; Zhong, P.; Lin, Q. L. Synthesis 2007, 85.
56. Tang, R. Y.; Zhong, P.; Lin, Q. L. Chin. J. Chem. 2007, 25, 558.
57. Krief, A.; Delmotte, C.; Dumont, W. Tetrahedron Lett. 1997, 38, 3079.
58. Phadnis, P. P.; Mugesh, G. Org. Biomol. Chem. 2005, 3, 2476.
59. All the aziridines were generally prepared from the corresponding alkenes: Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
60. The ratio of regioisomers was determined based on the integration values of 1H NMR. Lee, E.; Yoo, S. K.; Choo, H.; Song, H. Y. Tetrahedron Lett. 1998, 39, 317.
61. Purification of laboratory chemicals, 3rd Ed.; Perrin, D. D.; Armarego, W. L. F., Eds.; Pergamon Press: Oxford, 1998.
62. Braga, A. L.; Schwab, R. S.; Alberto, E. E.; Salman, S. M.; Vargas, J.; Azeredo, J. B. Tetrahedron Lett. 2009, 50, 2309.
63. Barton, D. H. R.; Britten-Kelly, M. R.; Ferreira, D. J. Chem. Soc., Perkin Trans. 1 1978, 9, 1090.
64. Gupta, V.; Besev, M.; Engman, L. Tetrahedron Lett. 1998, 39, 2429.
65. Engman, L. J. Org. Chem. 1987, 52, 4086.
66. Hu, Y.; Xi, Y.; Wang, J.; Du, Z.; Zhao, K. Synth. Commun. 2000, 30, 3101.
67. Kano, S.; Yokomatsu, T.; Shibuya, S. J. Org. Chem. 1989, 54, 513.
68. Luo, Z.; Hou, X.; Dai, L. Tetrahedron: Asymmetry 2007, 18, 443.
69. Schuetz, R. D. J. Am. Chem. Soc. 1951, 73, 1881.
70. Fan, R.; Hou, X. J. Org. Chem. 2003, 68, 726.
71. Albanese, D.; Landini, D.; Penso, M. Synthesis 1994, 34.
72. Minor, W. F.; Smith, R. R.; Cheney, L. C. J. Am. Chem. Soc. 1954, 76, 2993.