Tertiary amine-promoted enone aziridination: Investigations into factors influencing enantioselective induction

Tetrahedron Asymmetry

Volumn 25, Issue 1, 2014, Pages 74-86

  Armstrong, Alan ^a   Pullin, Robert D C ^a   Jenner, Chloe R ^a   Foo, Klement ^a   White, Andrew J P ^a   Scutt, James N ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; HYDRAZINE; KETONE DERIVATIVE; QUININE DERIVATIVE; TERTIARY AMINE;

ARTICLE; CATALYST; CONFORMATION; ENANTIOSELECTIVITY; NUCLEOPHILICITY; PRIORITY JOURNAL; PROMOTER REGION; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 84892551363     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2013.11.008     Document Type: Article

References (59)

1. For a review see: Lowden, P. A. S. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, Germany, 2006; p 399.
2. For a review see: (a) Muller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905;
3. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693;
4. (c) Pellissier, H. Tetrahedron 2010, 66, 1509;
5. (d) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
6. For a review see: (a) Kawabata, H.; Omura, K.; Uchida, T.; Katsuki, T. Chem. Asian J. 2007, 2, 248;
7. (b) Nishikori, H.; Katsuki, T. Tetrahedron Lett. 1996, 37, 9245;
8. (c) Nishimura, M.; Minakata, S.; Takahashi, T.; Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2002, 67, 2101;
9. (d) Subbarayan, V.; Ruppel, J. V.; Zhu, S.; Perman, J. A.; Zhang, X. P. Chem. Commun. 2009, 4266.
10. For selected examples see (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328;
11. (b) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450;
12. (c) Wang, X.; Ding, K. Chem. Eur. J. 2006, 12, 4568.
13. Ma, L.; Du, D.-M.; Xu, J. J. Org. Chem. 2005, 70, 10155.
14. Fukunaga, Y.; Uchida, T.; Ito, Y.; Matsumoto, K.; Katsuki, T. Org. Lett. 2012, 14, 4658.
15. For examples see (a) Aires-de-Sousa, J.; Lobo, A. M.; Prabhakar, S. Tetrahedron Lett. 1996, 37, 3183;
16. (b) Aires-de-Sousa, J.; Prabhakar, S.; Lobo, A. M.; Rosa, A. M.; Gomes, M. J. S.; Corvo, M. C.; Williams, D. J.; White, A. J. P. Tetrahedron: Asymmetry 2002, 12, 3349;
17. (c) Fioravanti, S.; Mascia, M. G.; Pellacani, L.; Tardella, P. A. Tetrahedron 2004, 60, 8073;
18. (d) Murugan, E.; Siva, A. Synthesis 2005, 2022;
19. (e) Minakata, S.; Murakami, Y.; Tsuruoka, R.; Kitanaka, S.; Komatsu, M. Chem. Commun. 2008, 6363.
20. For examples see: (a) Arai, H.; Sugaya, N.; Sasaki, N.; Makino, K.; Lectard, S.; Hamada, Y. Tetrahedron Lett. 2009, 50, 3329;
21. (b) Deiana, L.; Dziedzic, P.; Zhao, G.-L.; Vesely, J.; Ibrahem, I.; Rios, R.; Sun, J.; Córdova, A. Chem. Eur. J. 2011, 17, 7904;
22. (c) Deiana, L.; Zhao, G.-L.; Lin, S.; Dziedzic, P.; Zhang, Q.; Leijonmarck, H.; Córdova, A. Adv. Synth. Catal. 2010, 352, 3201;
23. (d) Desmarchelier, A.; Pereira de Sant'Ana, D.; Terrasson, V.; Campagne, J. M.; Moreau, X.; Greck, C.; Marcia de Figueiredo, R. Eur. J. Org. Chem. 2011, 4046;
24. (e) Vesely, J.; Ibrahem, I.; Zhao, G. L.; Rios, R.; Córdova, A. Angew. Chem., Int. Ed. 2007, 46, 778.
25. (a) Menjo, Y.; Hamajima, A.; Sasaki, N.; Hamada, Y. Org. Lett. 2011, 13, 5744;
26. (b) Jiang, H.; Holub, N.; Anker Jørgensen, K. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20630;
27. (c) De Vincentiis, F.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, A.; Bartoli, G.; Galzerano, P.; Melchiorre, P. Chem. Asian J. 2010, 5, 1652;
28. (d) Pesciaioli, F.; De Vincentiis, F.; Galzerano, P.; Bencivenni, G.; Bartoli, G.; Mazzanti, A.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8703.
29. Ikeda, I.; Machii, Y.; Okahara, M. Synthesis 1980, 650.
30. Armstrong, A.; Carbery, D. R.; Lamont, S. G.; Pape, A. R.; Wincewicz, R. Synlett 2006, 2504.
31. Xu, J.; Jiao, P. J. Chem. Soc., Perkin Trans. 1 2002, 1491.
32. Shen, Y.-M.; Zhao, M.-X.; Xu, J.; Shi, Y. Angew. Chem. Int. Ed. 2006, 45, 8005.
33. Armstrong, A.; Baxter, C. A.; Lamont, S. G.; Pape, A. R.; Wincewicz, R. Org. Lett. 2007, 9, 351.
34. Armstrong, A.; Ferguson, A. Beilstein. J. Org. Chem. 2012, 8, 1747.
35. Armstrong, A.; Pullin, R. D. C.; Jenner, C. R.; Scutt, J. N. J. Org. Chem. 2010, 75, 3499.
36. Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178.
37. Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559.
38. Dave, R.; Sasaki, N. A. Org. Lett. 2004, 6, 15.
39. Kawaguchi, M.; Ohashi, J.; Kawakami, Y.; Yamamoto, Y.; Oda, J. Synthesis 1985, 701.
40. Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Angew. Chem. Int. Ed. 2008, 47, 3784.
41. Johansson, C. C. C.; Bremeyer, N.; Ley, S. V.; Owen, D. R.; Smith, S. C.; Gaunt, M. J. Angew. Chem. Int. Ed. 2006, 45, 6024.
42. Hintermann, L.; Schmitz, M.; Englert, U. Angew. Chem. Int. Ed. 2007, 46, 5164.
43. Hutchison, D. R.; Khau, V. V.; Martinelli, M. J.; Nayyar, N. K.; Peterson, B. C.; Sullivan, K. A. Org. Synth. 1998, 75, 223.
44. Bucher, C.; Sparr, C.; Schweizer, W. B.; Gilmour, R. Chem. Eur. J. 2009, 15, 7637.
45. Braje, W. M.; Holzgrefe, J.; Wartchow, R.; Hoffmann, H. M. R. Angew. Chem. Int. Ed. 2000, 39, 2085.
46. Brunner, H.; Bügler, J.; Nuber, B. Tetrahedron Asymmetry 1995, 6, 1699.
47. Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Org. Lett. 2005, 7, 1967.
48. For a review see: Connon, S. J. Chem. Commun. 2008, 2499.
49. For aminocatalytic epoxidations of cyclic enones using salts of 23b see: Wang, X.; Reisinger, C. M.; List, B. J. Am. Chem. Soc. 2008, 130, 6070.
50. For aminocatalytic epoxidations of acyclic enones using salts of 23b see: Reisinger, C. M.; Wang, X. W.; List, B. Angew. Chem. Int. Ed. 2008, 47, 8112.
51. For a review see: Masson, G.; Housseman, C.; Zhu, J. Angew. Chem. Int. Ed. 2007, 46, 4614.
52. Nakano, A.; Kawahara, S.; Akamatsu, S.; Morokuma, K.; Nakatani, M.; Iwabuchi, Y.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Tetrahedron 2006, 62, 381.
53. (a) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H. J. Org. Chem. 1990, 55, 6121;
54. (b) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069.
55. Pniewska, B.; Suszko-Purzycka, A. Acta. Cryst. 1989, C45, 638.
56. Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 863857. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
57. Perdicchia, D.; Jørgensen, K. A. J. Org. Chem. 2007, 72, 3565.
58. Braga, A. L.; Paixão, M. W.; Westermann, B.; Schneider, P. H.; Wessjohann, L. A. J. Org. Chem. 2008, 73, 2879.
59. Demir, A. S.; Sesenoglu, Ö.; Ülkü, D.; Arici, C. Helv. Chim. Acta 2004, 87, 106.