Rh(II)-catalyzed Sommelet-Hauser rearrangement

Organic Letters

Volumn 10, Issue 5, 2008, Pages 693-696

  Liao, Mingyi ^a   Peng, Lingling ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 46949086340     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol703058p     Document Type: Article

References (54)

1. For reviews, see: (a) Trost, B. M.; Melvin, L. S., Jr. Sulfur Ylides; Academic Press: New York, 1975; Chapter 7.
2. (b) Vedejs, E. Acc. Chem. Res. 1984, 17, 358.
3. For seminal publications, see: (a) Sommelet, M. Compt. Rend. 1937, 205, 56.
4. (b) Kantor, S. W.; Hauser, C. R. J. Am. Chem. Soc. 1951, 73, 4122.
5. (c) Hauser, C. R.; Kantor, S. W.; Brasen, W. R. J. Am. Chem. Soc. 1953, 75, 2660.
6. For recent reviews, see: (a) Marko, I. E. In Compresive Organic Synthesis; Trost, B. M., Freming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 6, p 913.
7. (b) Beall, L. S.; Padwa, A. Adv. Nitrogen Heterocycl. 1998, 3, 117-158.
8. (c) Clark, J. S. Nitrogen, Oxygen, Sulfur Ylide Chem. 2002, 1-113.
9. For most recent examples, see: (a) Hanessian, S.; Talbot, C.; Saravanan, P. Synthesis 2006, 723.
10. (b) Tayama, E.; Kimura, H. Angew. Chem., Int. Ed. 2007, 46, 8869.
11. (a) Robert, A.; Thomas, M. T.; Foucaud, A. J. Chem. Soc., Chem. Commun. 1979, 1048.
12. (b) Jończyk, A.; Lipiak, D. J. Org. Chem. 1991, 56, 6933.
13. (c) Ishibashi, H.; Tabata, T.; Kobayashi, T.; Takamuro, I.; Ikeda, M. Chem. Pharm. Bull. 1991, 39, 2878.
14. (a) Hauser, C. R.; Van Eenam, D. N. J. Am. Chem. Soc. 1957, 79, 5512.
15. (b) Van Eenam, D. N.; Hauser, C. R. J. Am. Chem. Soc. 1957, 79, 5520.
16. (c) Hauser, C. R.; Van Eenam, D. N.; Bayless, P. L. J. Org. Chem. 1958, 23, 354.
17. (d) Shirai, N.; Sumiyama, F.; Sato, Y.; Hori, M. J. Org. Chem. 1989, 54, 836.
18. (e) Berger, R.; Ziller, J. W.; Van Vranken, D. L. J. Am. Chem. Soc. 1998, 120, 841.
19. (f) McComas, C. C.; Van Vranken, D. L. Tetrahedron Lett. 2003, 44, 8203.
20. Vedejs, E.; West, F. G. Chem. Rev. 1986, 86, 941.
21. (a) Nakano, M.; Sato, Y. J. Org. Chem. 1987, 52, 1844.
22. (b) Shirai, N.; Sato, Y. J. Org. Chem. 1988, 53, 194.
23. (c) Shirai, N.; Watanabe, Y.; Sato, Y. J. Org. Chem. 1990, 55, 2767.
24. (d) Sato, Y.; Shirai, N.; Machida, Y.; Ito, E.; Yasui, T.; Kurono, Y.; Hatano, K. J. Org. Chem. 1992, 57, 6711.
25. (e) Maeda, Y.; Shirai, N.; Sato, Y.; Tatewaki, H. J. Org. Chem. 1994, 59, 7897.
26. (f) Tanzawa, T.; Ichioka, M.; Shirai, N.; Sato, Y. J. Chem. Soc., Perkin Trans. 1 1995, 431.
27. (g) Tanzawa, T.; Shirai, N.; Sato, Y.; Hatano, K.; Kurono, Y. J. Chem. Soc., Perkin Trans. 1 1995, 2845.
28. Maeda, Y.; Sato, Y. J. Org. Chem. 1996, 61, 5188.
29. For reviews, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
30. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Inter-science: New York, 1998.
31. (c) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
32. (d) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
33. (e) Hodgson, O. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
34. For recent reports on transition metal-catalyzed sulfur ylide [1,2] shift, see: (a) Nair, V.; Nair, S. M.; Mathai, S.; Liebscher, J.; Ziemer, B.; Narsimulu, K. Tetrahedron Lett. 2004, 45, 5759.
35. (b) Ellis-Holder, K. K.; Peppers, B. P.; Kovalevsky, A. Y.; Diver, S. T. Org. Lett. 2006, 8, 2511.
36. (c) Stepakov, A. V.; Molchanov, A. P.; Magull, J.; Vidovic, D.; Starova, G. L.; Kopfc, J.; Kostikov, R. R. Tetrahedron 2006, 62, 3610.
37. For selected recent reports on transition metal-catalyzed sulfur ylide [2,3] sigmatropic rearrangement, see: (a) Novikov, A. V.; Kennedy, A. R.; Rainier, J. D. J. Org. Chem. 2003, 68, 993.
38. (b) Nyong, A. M.; Rainier, J. D. J. Org. Chem. 2005, 70, 746.
39. (c) Ma, M.; Peng, L.; Li, C.; Zhang, X.; Wang, J. J. Am. Chem. Soc. 2005, 127, 15016.
40. (d) Liao, M.; Wang, J. Green Chem. 2007, 9, 184.
41. For reviews, see: (a) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
42. (b) Fulton, J. R.; Aggarwal, V. K.; Vicente, J. D. Eur. J. Org. Chem. 2005, 1479.
43. Aggarwal, V. K.; Smith, H. W.; Hynd, G.; Jones, R. V. H.; Fieldhouse, R.; Spey, S. E. J. Chem. Soc., Perkin Trans. 1 2000, 3267.
44. For a recent study about competition between [1,2] Stevens and [2,3] Sommelet-Hauser rearrangement, see: Jończyk, A.; Lipiak, D.; Sienkiewicz, K. Synlett 1991, 493.
45. (a) Ollis, W. D.; Rey, M.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1983, 1009.
46. (b) Eberlein, T. H.; West, F. G.; Tester, R. W. J. Org. Chem. 1992, 57, 3479.
47. (a) Davies, H. M. L.; Hutcheson, D. K. Tetrahedron Lett. 1993, 34, 7243.
48. (b) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
49. Qu, Z.; Shi, W.; Wang, J. J. Org. Chem. 2001, 66, 8139.
50. To unambiguously establish the structure of product, 5d was converted to the corresponding sulfone, which was analyzed by X-ray crystallography, see the Supporting Information.
51. Similar selectivity has been recently reported in the ammonium ylide Sommelet-Hauser rearrangement, see ref 4b.
52. (a) Davies, H. M. L.; Bruzinski, P. R.; Fall, M. J. Tetrahedron Lett. 1996, 37, 4133.
53. (b) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
54. For a recent review, see: Smith, K.; El-Hiti, G. A. Curr. Org. Synth. 2004, 1, 253.