The reduction of α-silyloxy ketones using phenyldimethylsilyllithium

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 7, 1998, Pages 1215-1228

  Fleming, Ian ^a   Roberts, Richard S ^a   Smith, Stephen C ^b  

^a Department of Chemistry ^*  (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748813254     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a709114a     Document Type: Article

References (69)

1. E. J. Corey, M. A. Tius and J. Das, J. Am. Chem. Soc., 1980, 102, 1742.
2. I. Fleming and U. Ghosh, J. Chem. Soc., Perkin Trans. 1, 1994, 257.
3. I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1209.
4. H. J. Reich, R. C. Holtan and C. Bolm, J. Am. Chem. Soc., 1990, 112, 5609.
5. D. Wittenberg, T. C. Wu and H. Gilman, J. Org. Chem., 1959, 24, 1349;
6. E. Vedejs, M. J. Arnost, J. M. Eustache and G. A. Krafft, J. Org. Chem., 1982, 47, 4384;
7. G. A. Krafft and P. T. Meinke, J. Am. Chem. Soc., 1988, 110, 8671;
8. M. Koreeda and S. Koo, Tetrahedron Lett., 1990, 31, 831;
9. A. G. M. Barrett, J. M. Hill and E. W. Wallace, J. Org. Chem., 1992, 57, 386.
10. G. H. Dodd, B. T. Golding and P. V. Ioannou, J. Chem. Soc., Perkin Trans. 1, 1976, 2273.
11. D. J. Ager, Org. React. (N.Y.), 1990, 38, 1.
12. P. F. Hudrlik, R. H. Schwartz and A. K. Kulkarni, Tetrahedron Lett., 1979, 2233;
13. P. F. Hudrlik, G. Nagendrappa, A. K. Kulkarni and A. M. Hudrlik, Tetrahedron Lett., 1979, 2237.
14. M. S. Biernbaum and H. S. Mosher, J. Am. Chem. Soc., 1971, 93, 6221;
15. A. G. Brook and J. D. Pascoe, J. Am. Chem. Soc., 1971, 93, 6224.
16. P. F. Hudrlik, A. M. Hudrlik and A. K. Kulkarni, J. Am. Chem. Soc., 1982, 104, 6809;
17. S. R. Wilson, M. S. Hague and R. N. Misra, J. Org. Chem., 1982, 47, 747;
18. R. J. Linderman and A. Ghannam, J. Am. Chem. Soc., 1990, 112, 2392.
19. M. J. Tozer and T. F. Herpin, Tetrahedron, 1996, 52, 8619;
20. J. T. Welch, Tetrahedron, 1987, 43, 3123;
21. Selective Fluorination in Organic and Biological Chemistry, ed. J. T. Welch, ACS Symposium series 456, ACS, Washington DC, 1991;
22. M. H. Gelb, J. P. Svaren and R. H. Abeles, Biochemistry, 1985, 24, 1813;
23. S. Thaisrivongs, D. T. Pals, W. M. Kati, S. R. Turner, L. M. Thamasco and W. Watt, J. Med. Chem., 1986, 29, 2080;
24. M. H. Gelb, J. Am. Chem. Soc., 1986, 108, 3146.
25. M. Yamana, T. Ishihara and T. Ando, Tetrahedron Lett., 1983, 24, 507;
26. T. Ishihara, T. Yamanaka and T. Ando, Chem. Lett., 1984, 1165;
27. M. Kuroboshi and T. Ishihara, Tetrahedron Lett., 1987, 28, 6481;
28. M. Kuroboshi and T. Ishihara, Bull. Chem. Soc. Jpn., 1990, 63, 428;
29. K. Iseki, Y. Kuroki, D. Asada and Y. Kobayashi, Tetrahedron Lett., 1997, 38, 1447.
30. T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117;
31. C. Portella and B. Dondy, Tetrahedron Lett., 1991, 32, 83;
32. B. Dondy, P. Doussot and C. Portella, Synthesis, 1992, 995;
33. B. Dondy and C. Portella, J. Org. Chem., 1993, 58, 6671;
34. P. Doussot and C. Portella, J. Org. Chem., 1993, 58, 6675;
35. B. Dondy, P. Doussot and C. Portella, Tetrahedron Lett., 1994, 35, 409.
36. F. Jin, B. Jiang and Y. Xu, Tetrahedron Lett., 1992, 33, 1221;
37. F. Jin, Y. Xu and W. Huang, J. Chem. Soc., Perkin Trans. 1, 1993, 795.
38. H. Schubert, J. Prakt. Chem., 1956, 3, 146.
39. K. Rühlmann, Synthesis, 1971, 236.
40. B. B. Corson, W. L. Benson and T. T. Goodwin, J. Am. Chem. Soc., 1930, 52, 3988.
41. J. Cossy and P. Pale, Tetrahedron Lett., 1987, 28, 6039.
42. I. Dyong and H. P. Bertram, Chem. Ber., 1973, 106, 1743.
43. H. Teichmann and V. Prey, Justus Liebigs Ann. Chem., 1970, 732, 121.
44. G. J. D. Peddle, J. Organomet. Chem., 1967, 27, 2311.
45. G. A. Molander and G. Hahn, J. Org. Chem., 1986, 51, 1135.
46. W. Lidy and W. Sundermeyer, Chem. Ber., 1973, 106, 587.
47. R. Roger, J. Chem. Soc., 1925, 127, 518.
48. S. Hünig and G. Wehner, Chem. Ber., 1979, 112, 2062.
49. E. P. Kohler and J. L. E. Erickson, J. Am. Chem. Soc., 1931, 53, 2301.
50. M. Julia and M. Maumy, Org. Synth., 1988, Coll. Vol. 6, 586.
51. R. J. Bushby and G. J. Ferber, J. Chem. Soc., Perkin Trans. 2, 1976, 1683.
52. A. J. Bowers, T. G. Halsall, E. R. H. Jones and A. J. Lemin, J. Chem. Soc., 1953, 2548.
53. M. M. Shemyakin, L. A. Neiman, S. V. Zhokova, Y. S. Nekrasov, T. J. Pehk and E. T. Lippmaa, Tetrahedron, 1971, 27, 2811.
54. A. Jonczyk, M. Ludwikow and M. Makosza, Rocz. Chem., 1977, 51, 175.
55. G. Simchen and W. Kober, Synthesis, 1976, 259.
56. Handbook of Chemistry and Physics, The Chemical Rubber Publishing Co., Cleveland, Ohio, 52 edn., 1972.
57. D. S. Matteson and R. J. Moody, Organometallics, 1982, 1, 20.
58. D. S. MacNair, Justus Liebigs Ann. Chem., 1880, 258, 220.
59. M. G. Mayberry and J. G. Aston, J. Am. Chem. Soc., 1934, 56, 2682.
60. T.-L. Ho, Synthesis, 1972, 697.
61. V. Meyer and L. Oelkers, Ber., 1888, 21, 1295.
62. J. C. Lee Jr., C. G. Boojamra and R. H. Crabtree, J. Org. Chem., 1993, 58, 3895.
63. B. B. Corson and R. W. McAllister, J. Am. Chem. Soc., 1929, 51, 2822.
64. G. Berti and F. Bottari, J. Org. Chem., 1960, 25, 286.
65. F. Eisenlohr and L. Hill, Ber., 1937, 70, 942.
66. S. G. Cohen, H. T. Wolosinski and P. J. Scheuer, J. Am. Chem. Soc., 1949, 71, 3439.
67. C. Wakselman and J. Leroy, J. Chem. Soc., Chem. Commun., 1976, 611.
68. S. Sibille, E. d'Incan, L. Leport and J. Perichon, Tetrahedron Lett., 1986, 27, 3129.
69. M. Kuroboshi and T. Ishihara, Bull. Chem. Soc. Jpn., 1990, 63, 428.