Enantioselective haloetherification by asymmetric opening of meso -halonium ions

Organic Letters

Volumn 13, Issue 5, 2011, Pages 860-863

  Hennecke, Ulrich ^a   Müller, Christian H ^a   Fröhlich, Roland ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952149352     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1028805     Document Type: Article

References (49)

1. French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354
2. Chen, G.; Ma, S. Angew. Chem., Int. Ed. 2010, 49, 8306
3. Kitagawa, O; Hanano, T.; Tanabe, K.; Shiro, M.; Taguchi, T. J. Chem. Soc., Chem. Commun. 1992, 1005
4. Grossmann, R. B.; Trupp, R. J. Can. J. Chem. 1998, 76, 1233
5. Haas, J.; Piguel, S.; Wirth, T. Org. Lett. 2002, 4, 297
6. Hass, J.; Bissmire, S.; Wirth, T. Chem.-Eur. J. 2005, 11, 5777
7. Garnier, J. M.; Robin, S.; Rousseau, G. Eur. J. Org. Chem. 2007, 3281
8. For a related chiral pyridine/bromonium electrophile and its application, see: Cui, X. L.; Brown, R. S. J. Org. Chem. 2000, 56, 5653
9. Sakakura, A.; Ukai, A.; Ishihara, K. Nature 2007, 445, 900
10. Kang, S. H.; Sung, B. L.; Park, C. M. J. Am. Chem. Soc. 2003, 125, 15748
11. Kwon, H. Y.; Park, C. M.; Sung, B. L.; Youn, J.-H.; Kang, S. H. Chem.-Eur. J. 2008, 14, 1023
12. Kang, S. H.; Park, C. M.; Lee, S. B.; Kim, M. Synlett 2004, 1279
13. For a recent application of this catalyst system to iodolactonizations, see: Ning, Z.; Jin, R.; Ding, J.; Gao, L. Synlett 2009, 2291
14. Whitehead, D. C.; Yousefi, R.; Jaganathan, A.; Borhan, B. J. Am. Chem. Soc. 2010, 132, 3298
15. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332
16. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474
17. Murai, K.; Matsushita, T.; Nakamura, A.; Fukushima, S.; Shimura, M.; Fujioka, H. Angew Chem. Int. Ed. 2010, 49, 9174
18. Zhang, W.; Zheng, S.; Liu, N.; Werness, J. B.; Guzei, I. A.; Tang, W. J. Am. Chem. Soc. 2010, 132, 3664
19. Ahmad, S. M.; Braddock, D. C.; Cansell, G.; Hermitage, S. A.; Redmond, J. M.; White, A. J. P. Tetrahedron Lett. 2007, 48, 5948
20. Wang, M.; Gao, L. X.; Mai, W. P.; Xia, A. X.; Wang, F.; Zhang, S. B. J. Org. Chem. 2004, 69, 2874
21. For an extensive study of achiral Lewis base catalysis in halocyclization reactions, see: Denmark, S. E.; Burk, M. T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20655
22. Neverov, A. A.; Brown, R. S. J. Org. Chem. 1996, 61, 962
23. Denmark, S. E.; Burk, M. T.; Hoover, A. J. J. Am. Chem. Soc. 2010, 132, 1232
24. For related work on thiiranium and seleniranium ions, see: Denmark, S. E.; Collins, W. R.; Cullen, M. D. J. Am. Chem. Soc. 2009, 131, 3490
25. Braddock, D. C.; Hermitage, S. A.; Kwok, L.; Pouwer, R.; Redmond, J. M.; White, A. J. P. Chem. Commun. 2009, 1082
26. For a related study on thiiranium and seleniranium ions, see: Denmark, S. E.; Vogler, T. Chem.-Eur. J. 2009, 15, 11737
27. For related desymmetrization reactions of aziridines and thiiranium ions, see: Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084
28. Hamilton, G. L.; Kanai, T.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 14984-14986
29. Larson, S. E.; Baso, J. C.; Li, G.; Antilla, J. C. Org. Lett. 2009, 11, 5186 For chiral counter anion catalysis in general, see: Lacour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373
30. Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193-4195
31. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496
32. Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404
33. Rueping, M.; Antonchick, A. P.; Brinkmann, C. Angew. Chem., Int. Ed. 2007, 46, 6903
34. Lacour, J.; Moraleda, D. Chem. Commun. 2009, 7073
35. Trace amounts of water led to lower enantioselectivities.
36. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int Ed. 2004, 43, 1566
37. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356
38. Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696
39. Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84
40. Kajigaeshi, S.; Kakinami, T.; Yamasaki, H.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn. 1988, 61, 600
41. For details on the preparation see Supporting Information.
42. See Supporting Information for details.
43. For BINOL-phosphates salts as Lewis acids, see: Inanaga, J.; Sugimoto, Y.; Hanamoto, T. New J. Chem. 1995, 19, 707
44. Furuno, H.; Hanamoto, T.; Sugimoto, Y.; Inanaga, J. Org. Lett. 2000, 2, 49
45. Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem.-Eur. J. 2010, 16, 9350
46. For an application of a chiral sodium phosphate, see: Shen, K.; Liu, X.; Cai, Y.; Lin, L.; Feng, X. Chem.-Eur. J. 2009, 15, 6008
47. 2, see Supporting Information for details). For complexes of halide anions with NIS, see: Eberson, L.; Finkelstein, M.; Folkesson, B.; Hutchins, G. A.; Jönsson, L.; Larsson, R.; Moore, W. M.; Ross, S. D. J. Org. Chem. 1986, 51, 4400
48. Ghassemzadeh, M.; Dehnicke, K.; Goesmann, H.; Fenske, D. Z. Naturforsch. 1994, 49b, 602
49. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 49, 1560