Synthesis of deuterium labeled compounds by KCN-assisted hydrolysis of phosphonium salts

Tetrahedron Letters

Volumn 45, Issue 31, 2004, Pages 5977-5981

  Lee, Ka Young ^a   Na, Jeong Eun ^a   Lee, Mi Jung ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Deuterium labeled compounds; KCN; Phosphonium salts

Indexed keywords

DEUTERIUM; PHOSPHONIUM DERIVATIVE;

ARTICLE; HYDROLYSIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 3142656611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.058     Document Type: Article

References (69)

1. For the importance of D-labeled compounds in mechanistic study, see: Adam W., Bottke N., Krebs O., Lykakis I., Orfanopoulos M., Stratakis M. J. Am. Chem. Soc. 124:2002;14403
2. Abe M., Adam W., Ino Y., Nojima M. J. Am. Chem. Soc. 122:2000;6508
3. Abe M., Adam W., Minamoto T., Ino Y., Nojima M. J. Org. Chem. 68:2003;1796
4. Hayashi T., Yamasaki K., Mimura M., Uozumi Y. J. Am. Chem. Soc. 126:2004;3036
5. Baldwin J.E., Leber P.A. J. Am. Chem. Soc. 123:2001;8396
6. Adam W., Krebs O., Orfanopoulos M., Stratakis M. J. Org. Chem. 67:2002;8395
7. Johnstone R.A.W., Price P.J. Tetrahedron. 41:1985;2493
8. For the study of biological pathways, see: Goese M., Eisenreich W., Kupfer E., Stohler P., Weber W., Leuenberger H.G., Bacher A. J. Org. Chem. 66:2001;4673
9. Kreck M., Puschel S., Wust M., Mosandl A. J. Agric. Food Chem. 51:2003;463
10. Millet O., Muhandiram D.R., Skrynnikov N.R., Kay L.E. J. Am. Chem. Soc. 124:2002;6439
11. Gu S., Pan S., Bradbury E.M., Chen X. Anal. Chem. 74:2002;5774
12. Zhang Y.H., Yan X., Maier C.S., Schimerlik M.I., Deinzer M.L. Biochemistry. 41:2002;15495
13. Proteay P.J. Tetrahedron Lett. 39:1998;9373
14. Prabhakaran P.C., Woo N.-T., Yorgey P., Gould S.J. Tetrahedron Lett. 27:1986;3815
15. Rock D.A., Boitano A.E., Wahlstrom J.L., Rock D.A., Jones J.P. Bioorg. Chem. 30:2002;107
16. For the importance of D-labeled compounds in structural determinations, see: Zeng X.B., Ungar G. Macromolecules. 36:2003;4686
17. Bateman J.E., Eagling R.D., Horrocks B.R., Houlton A. J. Phys. Chem. B. 104:2000;5557
18. Amelung W., Brodowski S. Anal. Chem. 74:2002;3239
19. Yu X., Pawliszyn J. Anal. Chem. 72:2000;1788
20. Brotin T., Lesage A., Emsley L., Collet A. J. Am. Chem. Soc. 122:2000;1171
21. Adams C.H., Brereton M.G., Hutchings L.R., Klein P.G., McLeish T.C.B., Richards R.W., Ries M.E. Macromolecules. 33:2000;7101
22. For the introduction of deuterium atom into organic compounds, see: Sajiki H., Aoki F., Esaki H., Maegawa T., Hirota K. Org. Lett. 6:2004;1485
23. Concellon J.M., Rodriguez-Solla H., Concellon C. Tetrahedron Lett. 45:2004;2129
24. Skaddan M.B., Yung C.M., Bergman R.G. Org. Lett. 6:2004;11
25. Weigelt S., Sewald N. Synlett. 2004;726
26. Concellon J.M., Rodriguez-Solla H. Chem. Eur. J. 8:2002;4493
27. Eames J., Coumbarides G.S., Suggate M.J., Weerasooriya N. Eur. J. Org. Chem. 2003;634
28. Concellon J.M., Bardales E., Llavona R. J. Org. Chem. 68:2003;1585
29. Labuschagne A.J.H., Schneider D.F. Tetrahedron Lett. 24:1983;743
30. Shattuck J.C., Meinwald J. Tetrahedron Lett. 38:1997;8461
31. Lygo B., Humphreys L.D. Tetrahedron Lett. 43:2002;6677
32. Audia J.E., Colocci N. Tetrahedron Lett. 32:1991;3779
33. Duralski A.A., Watts A. Tetrahedron Lett. 33:1992;4983
34. Theobald P.G., Okamura W.H. Tetrahedron Lett. 28:1987;6565
35. Chin T.-S., Wolinska-Mocydlarz J., Leitch L.C. J. Labelled Compds. 6:1970;285
36. Lauer W.M., Koons C.B. J. Org. Chem. 24:1959;1169
37. Yao J., Evilia R.F. J. Am. Chem. Soc. 116:1994;11229
38. Hanzlik R.P., Schaefer A.R., Moon J.B., Judson C.M. J. Am. Chem. Soc. 109:1987;4926
39. For the hydrolysis of phosphonium salts, see: Johnson A.W., Kaska W.C., Starzewski K.A.O., Dixon D.A. Ylides and Imines of Phosphorus. 1993;John Wiley & Sons, New York
40. Zanger M., VanderWerf C.A., McEwen W.E. J. Am. Chem. Soc. 81:1959;3806
41. Fenton G.W., Ingold C.K. J. Chem. Soc. 1929;2342
42. Horner L., Hoffmann H., Wippel H.G., Hassel G. Chem. Ber. 91:1958;52
43. Hoffmann H. Annalen. 634:1960;1
44. Aksnes G., Songstad J. Acta Chem. Scand. 16:1962;1426
45. Hudson R.F., Green M. Angew. Chem., Int. Ed. Engl. 2:1963;11
46. McEwen W.E. Topics Phosphorus Chem. 2:1965;1
47. Luckenbach R. Phosphorus. 1:1972;223
48. McEwen W.E., Kumli K.F., Blade-Font A., Zanger M., VanderWerf C.A. J. Am. Chem. Soc. 86:1964;2378
49. McClelland R.A., McGall G.H., Patel G. J. Am. Chem. Soc. 107:1985;5204
50. Gilheany D.G., Kelly P.G., Mitchell C.A., Walker B.J., Malone J.F., Blaney J., Wilson R. Phosphorus Sulfur Silicon. 75:1993;11
51. Cristau H.-J., Mouchet P. Phosphorus Sulfur Silicon. 107:1995;135
52. Gilheany D.G., Thompson N.T., Walker B.J. Tetrahedron Lett. 28:1987;3843
53. Corfield J.R., Trippett S. Chem. Commun. 1970;1267
54. Allen D.A., Grayson S.J., Harness I., Hutley B.G., Mowat I.W. J. Chem. Soc., Perkin Trans. 2. 1973;1912
55. Schlosser M. Chem. Ber. 97:1964;3219
56. Schnell A., Tebby J.C. J. Chem. Soc., Perkin Trans. 1. 9:1977;1883
57. Im Y.J., Na J.E., Kim J.N. Bull. Korean Chem. Soc. 24:2003;511
58. For our recent publications on the Baylis-Hillman reaction, see: Kim J.M., Lee K.Y., Lee S.-k., Kim J.N. Tetrahedron Lett. 45:2004;2805
59. Lee K.Y., Kim J.M., Kim J.N. Tetrahedron Lett. 44:2003;6737
60. Kim J.N., Kim J.M., Lee K.Y. Synlett. 4:2003;821
61. Im Y.J., Lee C.G., Kim H.R., Kim J.N. Tetrahedron Lett. 44:2003;2987
62. Lee K.Y., Kim J.M., Kim J.N. Synlett. 9:2003;357
63. Kim J.N., Lee H.J., Lee K.Y., Gong J.H. Synlett. 2002;173
64. Chung Y.M., Gong J.H., Kim T.H., Kim J.N. Tetrahedron Lett. 42:2001;9023
65. Im Y.J., Kim J.M., Mun J.H., Kim J.N. Bull. Korean Chem. Soc. 22:2001;349
66. Lee K.Y., Kim J.M., Kim J.N. Tetrahedron. 59:2003;385. and references cited therein
67. +, 100)
68. 6) δ 5.29 (d, J=15.6 Hz, 4H), 7.04 (d, J=8.1 Hz, 4H), 7.52 (d, J=8.1 Hz, 4H), 7.50-7.92 (m, 30H)
69. 6) δ 1.82 (m, 2H), 2.82 (m, 2H), 7.15-7.21 (m, 3H), 7.25-7.31 (m, 2H), 7.74-7.95 (m, 15H)