Efficient synthesis of α-tertiary α-silylamines from aryl sulfonylimidates via one-pot, sequential C-Si/C-C bond formations

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2906-2909

  Han, Xiao Jun ^a,b   Yao, Ming ^a,b   Lu, Chong Dao ^a,b  

^a XINJIANG TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LITHIUM; ORGANOMETALLIC COMPOUND; ORGANOSILICON DERIVATIVE; PHENYLDIMETHYLSILYLLITHIUM; SULFONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINES; CATALYSIS; INDICATORS AND REAGENTS; LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOSILICON COMPOUNDS; STEREOISOMERISM; SULFONES;

EID: 84861818014     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301194e     Document Type: Article

References (60)

1. For a review of the chemistry and biological activities of silylmethylamines and their derivatives, see: Picard, J.-P. Adv. Organomet. Chem. 2005, 52, 175
2. Noll, J. E.; Speier, J. L.; Daubert, B. F. J. Am. Chem. Soc. 1951, 73, 3867
3. Sommer, L. H.; Rocket, J. J. Am. Chem. Soc. 1951, 73, 5130
4. Ramon, D. J.; Yus, M. Curr. Org. Chem. 2004, 8, 149
5. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268
6. Davis, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 65, 8704
7. Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Org. Chem. 2002, 67, 5359
8. Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686
9. Dhudshia, B.; Tiburcio, J.; Thadani, A. N. Chem. Commun. 2005, 5551
10. Garcia Ruano, J. L.; Aleman, J.; Parra, A. J. Am. Chem. Soc. 2005, 127, 13048
11. Lauzon, C.; Charette, A. B. Org. Lett. 2006, 8, 2743
12. Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687
13. Canales, E.; Hernandez, E.; Soderquist, J. A. J. Am. Chem. Soc. 2006, 128, 8712
14. Wang, J.; Hu, X.; Jiang, J.; Gou, S.; Huang, X.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2007, 46, 8468
15. Wang, J.; Wang, W.; Li, W.; Hu, X.; Shen, K.; Tan, C.; Liu, X.; Feng, X. Chem.-Eur. J. 2009, 15, 11642
16. Shintani, R.; Takeda, M.; Tsuji, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 13168
17. The addition of dimethylphenylsilyllithium to acetophenone-derived imine to afford the desired silylmethylamine in 11% yield: Ballweg, D. M.; Miller, R. C.; Gray, D. L.; Scheidt, K. A. Org. Lett. 2005, 7, 1403
18. The addition of diphenylmethylsilyllithium to acetone-derived imine gives a 31% yield: Nielsen, L.; Lindsay, K. B.; Faber, J.; Nielsen, N. C.; Skrydstrup, T. J. Org. Chem. 2007, 72, 10035
19. Vyas, D. J.; Fröhlich, R.; Oestreich, M. Org. Lett. 2011, 13, 2094
20. Suginome, M.; Matsuda, T.; Ito, Y. Organometallics 2000, 19, 4647
21. Brook, A. G.; Yu, Z. Organometallics 2000, 19, 1859
22. Brook, A. G.; Golino, C.; Matern, E. Can. J. Chem. 1978, 56, 2286
23. Yao, M.; Lu, C.-D. Org. Lett. 2011, 13, 2782
24. Liu, B.; Lu, C.-D. J. Org. Chem. 2011, 76, 4205
25. Adams, R.; Reifschneider, W. J. Am. Chem. Soc. 1956, 78, 3825
26. Reetz, M. T.; Westermann, J. J. Org. Chem. 1983, 48, 254
27. Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968
28. Murai, T.; Asai, F. J. Am. Chem. Soc. 2007, 129, 780
29. Agosti, A.; Britto, S.; Renaud, P. Org. Lett. 2008, 10, 1417
30. Murai, T.; Ui, K.; Narengerile J. Org. Chem. 2009, 74, 5703
31. Larouche-Gauthier, R.; Bélanger, G. Org. Lett. 2008, 10, 4501
32. Xiao, K.-J.; Luo, J.-M.; Ye, K.-Y.; Wang, Y.; Huang, P.-Q. Angew. Chem., Int. Ed. 2010, 49, 3037
33. Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N. Angew. Chem., Int. Ed. 2010, 49, 6369
34. Seebach, D. Angew. Chem., Int. Ed. 2011, 50, 96 and references therein
35. Vincent, G.; Guillot, R.; Kouklovsky, C. Angew. Chem., Int. Ed. 2011, 49, 3037
36. Cervinka, O. Collect. Czech. Chem. Commun. 1959, 24, 1146
37. Lukes, R.; Cerny, M. Collect. Czech. Chem. Commun. 1961, 26, 2886
38. Sernmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507
39. Zezza, C. A.; Smith, M. B.; Ross, B. A.; Arhin, A.; Cronin, P. L. E. J. Org. Chem. 1984, 49, 4397
40. Substitutions of the cyano group in 1-piperidinocyclohexanecarbonitrile by arylmagnesium halides have been described; see: Maddox., H.; Godefroi, E. E.; Parcell, R. F. J. Med. Chem. 1965, 8, 230
41. Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans. 1 1981, 2527
42. George, M. V.; Peterson, D. J.; Gilman, H. J. Am. Chem. Soc. 1960, 82, 403
43. Fleming, I. In Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; p 257.
44. Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Org. Lett. 2008, 10, 1727
45. Herrmann, A. T.; Martinez, S. R.; Zakarian, A. Org. Lett. 2011, 13, 3636
46. Similarly, methyl N -Tf-phenylimidate underwent the addition reaction and gave phenyl acylsilane 5 in 84% yield. This method for synthesizing aryl acylsilanes can be considered complementary to Scheidt's protocol. Scheidt's protocol is efficient for preparing alkyl acylsilanes using silyllithium species; however, it offers limited possibilities for aryl acylsilanes due to the undesired Brook rearrangement and subsequent transformations. See: Clark, C. T.; Milgram, B. C.; Scheidt, K. A. Org. Lett. 2004, 6, 3977
47. Brook, A. G.; Duff, J. M. J. Am. Chem. Soc. 1974, 96, 4692
48. Duff, J. M.; Brook, A. G. Can. J. Chem. 1977, 55, 2589
49. Yoshida, K.; Yamaguchi, K.; Sone, T.; Unno, Y.; Asai, A.; Yokosawa, H.; Matsuda, A.; Arisawa, M.; Shuto, S. Org. Lett. 2008, 10, 3571
50. Almansa, R.; Guijarro, D.; Yus, M. Tetrahedron 2009, 50, 4188
51. For review, see: Mortensen, M.; Husmann, R.; Veri, E.; Bolm, C. Chem. Soc. Rev. 2009, 38, 1002
52. For differences in reaction behavior of freshly prepared and commercially available vinylMgBr, see: Ushakov, D. B.; Navickas, V.; Strobele, M.; Maichle-Mossmer, C.; Sasse, F.; Maier, M. E. Org. Lett. 2011, 13, 2090
53. Evans, D. A.; Borg, G.; Scheidt, K. A. Angew. Chem., Int. Ed. 2002, 41, 3188 and references therein
54. Hatano, M.; Suzuki, S.; Ishihara, K. J. Am. Chem. Soc. 2006, 128, 9998
55. Tramontini, M. Synthesis 1982, 605
56. Hevia, E.; Chua, J. Z.; Garcia-Alvarez, P.; Kennedy, A. R.; McCall, M. D. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 5294
57. Gilman, H.; Lichtenwalter, G. D. J. Am. Chem. Soc. 1958, 80, 607
58. George, M. V.; Peterson, D. J.; Gilman, H. J. J. Am. Chem. Soc. 1960, 82, 403
59. Magnus, P.; Moursounidis, J. J. Org. Chem. 1991, 56, 1529
60. Still, W. C. J. Org. Chem. 1976, 41, 3063