Samarium diiodide-promoted electrophilic amination of ketone enolates: efficient synthesis of quaternary carbon-containing α-aminated ketones

Tetrahedron Letters

Volumn 49, Issue 40, 2008, Pages 5807-5809

  Sun, Xing Wen ^a   Wang, Wei ^a   Xu, Ming Hua ^a,b   Lin, Guo Qiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOKETONE; CARBON; KETONE DERIVATIVE; LITHIUM; SAMARIUM DIIODIDE;

AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ROOM TEMPERATURE;

EID: 49649109493     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.123     Document Type: Article

References (71)

1. For several review articles:. Erdik E., and Ay M. Chem. Rev. 89 (1989) 1947
2. Mulzer J. Organic Synthesis Highlights (1991), Wiley-VCH, Weinheim 45
3. Greck C., and Genet J.P. Synlett (1997) 741
4. Genet J.P., Greck C., and Lavergne D. Modern Amination Methods. In: Ricci A. (Ed) (2000), Wiley-VCH, Weinheim 65
5. Dembech P., Seconi G., and Ricci A. Chem. Eur. J. 6 (2000) 1281
6. Greck C., Drouillat B., and Thomassigny C. Eur. J. Org. Chem. (2004) 1377
7. Erdik E. Tetrahedron 60 (2004) 8747
8. Harmon R.E., Wellman G., and Gupta S.K. J. Org. Chem. 38 (1973) 11
9. Evans D.A., Britton T.C., Ellman J.A., and Dorrow R.L.L. J. Am. Chem. Soc. 112 (1990) 4011
10. Lwowski W., and Maricich J.M. J. Am. Chem. Soc. 87 (1965) 3630
11. Felice E., Fioravanti S., Pellacani L., and Tardella P.A. Tetrahedron Lett. 40 (1999) 4413
12. Greck C., Bischoff L., erreira F., and Genet J.P. J. Org. Chem. 60 (1995) 7010
13. Bernardi P., Dembech P., Fabbri G., Ricci A., and Seconi G. J. Org. Chem. 64 (1999) 641
14. Berman A.M., and Johnson J.S. J. Am. Chem. Soc. 126 (2004) 5680
15. Campbell M.J., and Johnson J.S. Org. Lett. 9 (2007) 1521
16. Carpino L.A., Terry P.H., and Crowley D.J. J. Org. Chem. 26 (1961) 4336
17. Lenarsic R., Kocevar M., and Polane S. J. Org. Chem. 64 (1999) 2558
18. Harris J.M., Bolessa E.A., Mendonca A.J., Feng S.-C., and Vederas J.C. J. Chem. Soc., Perkin Trans. 1 (1995) 1945
19. Meseguer M., Moreno-Mañas M., and Vallribera A. Tetrahedron Lett. 41 (2000) 4093
20. Andreae S., and Schmitz E. Synthesis (1991) 327
21. Shustov G.V., Kadorkina G.K., Varlamov S.V., Kachanov A.V., Kostyanovsky R.G., and Rauk A. J. Am. Chem. Soc. 114 (1992) 1616
22. Hannachi J.C., Vidal J., Mulatier J.C., and Collet A. J. Org. Chem. 69 (2004) 2367
23. Armstrong A., Edmonds I.D., Swarbrick M.E., and Treweeke N.R. Tetrahedron 61 (2005) 8423
24. Oppolzer W., and Tamura O. Tetrahedron Lett. 31 (1990) 991
25. Oppolzer W., Tamura O., Sundarababu G., and Signer M. J. Am. Chem. Soc. 114 (1992) 5900
26. Sapountzis I., and Knochel P. Angew. Chem., Int. Ed. 43 (2004) 897
27. Sinha P., Kofink C.C., and Knochel P. Org. Lett. 8 (2006) 3741
28. Mayer D. In: Müller E. (Ed). Houben Weyl, Methods of Organic Chemistry. fourth ed. vol. 7/2c (1977), Thieme Medical Publishers 2253
29. For recent examples:. List B. J. Am. Chem. Soc. 124 (2002) 5656
30. Bogevig A., Juhl K., Kumaragurubaran N., Zhuang W., and Jørgensen K.A. Angew. Chem., Int. Ed. 41 (2002) 1790
31. Duthaler R.O. Angew. Chem., Int. Ed. 42 (2003) 975
32. Dessole G., Bernardi L., Bonini B.F., Capitò E., Fochi M., Herrera R.P., Ricci A., and Cahiez G. J. Org. Chem. 69 (2004) 8525
33. Xu X., Yabuta T., Yuan P., and Takemoto Y. Synlett (2006) 137
34. Thomassigny C., Prim D., and Greck C. Tetrahedron Lett. 47 (2006) 1117
35. Kang Y.K., and Kim D.Y. Tetrahedron Lett. 47 (2006) 4565
36. Terada M., Nakano M., and Ube H. J. Am. Chem. Soc. 128 (2006) 16044
37. Liu T.-Y., Cui H.-L., Zhang Y., Jiang K., Du W., He Z.-Q., and Chen Y.-C. Org. Lett. 9 (2007) 3671
38. For a related, minireview see:. Janey J.M. Angew. Chem., Int. Ed. 44 (2005) 4292
39. Selected examples:. Trimble L.A., and Vederas J.C. J. Am. Chem. Soc. 108 (1986) 6397
40. Estermann H., and Seebach D. Helv. Chim. Acta 71 (1988) 1824
41. Enders D., Poiesz C., and Joseph R. Tetrahedron: Asymmetry 9 (1998) 3709
42. Page P.C.B., McKenzie M.J., Allin S.M., and Buckle D.R. Tetrahedron 56 (2000) 9683
43. Evans D.A., Britton T.C., Dorow R.L., and Dellaria J.F. J. Am. Chem. Soc. 108 (1986) 6395
44. Gmeiner P., and Bollinger B. Tetrahedron 50 (1994) 10909
45. Enders D., Joseph R., and Poiesz C. Tetrahedron 54 (1998) 10069
46. Gennari C., Colombo L., and Bertolini G. J. Am. Chem. Soc. 108 (1986) 6394
47. Evans D.A., and Johnson D.S. Org. Lett. 1 (1999) 595
48. 2 in organic synthesis, see:. Molander G.A. Chem. Rev. 92 (1992) 29
49. Molander G.A., and Harris C.R. Chem. Rev. 96 (1996) 307
50. Molander G.A., and Harris C.R. Tetrahedron 54 (1998) 3321
51. Skrydstrup T. Angew. Chem., Int. Ed. 36 (1997) 345
52. Krief A., and Laval A.M. Chem. Rev. 99 (1999) 745
53. Kagan H.B. Tetrahedron 59 (2003) 10351
54. Edmonds D.J., Johnston D., and Procter D.J. Chem. Rev. 104 (2004) 3371
55. Gopalaiah K., and Kagan H.B. New J. Chem. 32 (2008) 607
56. Xu M.-H., Wang W., and Lin G.-Q. Org. Lett. 2 (2000) 2229
57. Xu M.-H., Wang W., Xia L.-J., and Lin G.-Q. J. Org. Chem. 66 (2001) 3953
58. Wang W., Zhong Y.-W., and Lin G.-Q. Tetrahedron Lett. 44 (2003) 4613
59. Zhong Y.-W., Izumi K., Xu M.-H., and Lin G.-Q. Org. Lett. 6 (2004) 4747
60. Zhong Y.-W., Xu M.-H., and Lin G.-Q. Org. Lett. 6 (2004) 3953
61. Huang L.-L., Xu M.-H., and Lin G.-Q. J. Org. Chem. 70 (2005) 529
62. Zhong Y.-W., Dong Y.-Z., Fang K., Xu M.-H., and Lin G.-Q. J. Am. Chem. Soc. 127 (2005) 12956
63. Zhu C., Shi Y., Xu M.-H., and Lin G.-Q. Org. Lett. 10 (2008) 1243
64. For a samarium enolate example:. Wang W., Xu M.-H., Lei X.-S., and Lin G.-Q. Org. Lett. 2 (2000) 3773
65. Molander G.A., and Hahn G. J. Org. Chem. 51 (1986) 1135
66. Nakamura Y., Takeuchi S., Ohgo S., Yamaoka M., Yoshida A., and Mikami K. Tetrahedron 55 (1999) 4595
67. 2 chemistry, see:. Otsubo K., Inanaga J., and Yamaguchi M. Tetrahedron Lett. 27 (1986) 5763
68. Shabangi M., Sealy J.M., and Flowers II R.A. Tetrahedron Lett. 39 (1998) 4429
69. Hou Z., and Wakatsuki Y. J. Chem. Soc., Chem. Commun. (1994) 1205
70. Enemaerke R.J., Hertz T., Skrydstrup T., and Daasbjerg K. Chem. Eur. J. 6 (2000) 3747
71. 5: C, 65.32; H, 7.97; N, 6.93. Found