Stereoselective generation and trapping of lithium eneselenolates leading to ketene selenothioacetals and selenothioesters

Tetrahedron

Volumn 52, Issue 8, 1996, Pages 2839-2846

  Murai, Toshiaki ^a   Kakami, Kaori ^a   Itoh, Naoshi ^a   Kanda, Takahiro ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ESTER DERIVATIVE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030065871     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00005-1     Document Type: Article

References (52)

1. For reviews: (a) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Baldwin, J. E., Ed.; Pergamon Press: 1986.
2. (b) The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1987; Vol. 1 and 2.
3. (c) Organoselenium Chemistry, Liotta, D. Ed., Wiley-Interscience, New York, 1987, p 277.
4. Deryagina, E. N.; Voronkov, M. G.; Korchevin, N. A. Russ. Chem. Rev. 1993, 62, 1107.
5. (a) Barton, D. H. R.; Hanse, P.-E.; Picker, K. J. Chem. Soc., Perkin I 1977, 1723.
6. (b) Sukhai, R. S; Brandsma, L. Synthesis, 1979, 455.
7. (c) Sekiguchi, M.; Ogawa, A.; Fujiwara, S.; Ryu, I.; Kambe, N.; Sonoda, N. Chem. Lett. 1990, 2053.
8. (d) Kato, S.; Komuro, T.; Kanda, T.; Ishihara, H., Murai, T. J. Am. Chem. Soc. 1993, 115, 3000.
9. (e) Ogawa, A.; Sonoda, N. Rev. Heteroatom Chem. 1994, 10, 43.
10. (f) Kanda, T.; Ezaka, T.; Murai, T.; Kato, S. Tetrahedron Lett. 1995, 36, 2807.
11. (a) Kato, S.; Ishida, M. Sulfur Report 1988, 8, 155.
12. (b) Metzner, P. Synthesis 1992, 1185.
13. (c) Murai, T.; Kato, S. Comprehensive Organic Functional Group Transformations, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds. Pergamon, 1995, Vol. 5, Chapter 5.13 and references cited therein.
14. (a) Krafft, G. R.; Meinke, P. T. J. Am. Chem. Soc. 1986, 108, 1314.
15. (b) Meinke, G. A.; Krafft, G. A. Tetrahedron Lett. 1987, 28, 5121.
16. Meinke, P. T.; Krafft, G. A. J. Am. Chem. Soc. 1988, 110, 8671.
17. Segi, M.; Nakajima, T.; Suga, S.; Murai, S.; Ryu, I.; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1988, 110, 1976.
18. (e) Segi, M.; Koyama, T.; Nakajima, T.; Suga, S.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1989, 30, 2095.
19. (f) Takikawa, Y.; Uwano, A.; Watanabe, H.; Asanuma, M. Tetrahedron Lett. 1989, 30, 6047.
20. (g) Shimada, K.; Jin, N.; Fujimura, M.; Nagano, Y.; Kudoh, E.; Takikawa, Y. Tetrahedron Lett. 1992, 1843.
21. (a) Kato, S.; Murai, T.; Ishida, M. Org. Prep. Proceds. Int., 1986, 18, 369.
22. (b) Guziec, F. S. Jr. in Organoselenium Chemistry, Ed. Liotta, D. Wiley-Interscience, New York, 1987; Vol. 2, p 277.
23. (c) Gunziec, F. S. Jr. in The Chemistry of Organic Selenium and Tellurium Compounds, Ed. Patai, S. Jon Wiley & Sons Ltd., London, 1987, Vol. 1, p 215.
24. (d) Okazaki, R. J. Synth. Org. Chem.. Jpn. 1988, 46, 1149.
25. (e) Ogawa, A.; Sonoda, N. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds. Pergamon Press: Oxford, 1991; Vol. 6, Chapter 2.6.
26. (d) Segi, M.; Nakajima, T. J. Synth. Org. Chem. Japan 1995, 53, 678.
27. For recent examples of the synthesis of enolizable selenoamides; (a) Malek-Yazdi, F.; Yalpani, M. Synthesis, 1977, 328.
28. (b) Sukhai, R. S.; Jong, R.; Brandsma, L. Synthesis, 1977, 888.
29. (c) Cohen, V. I. J. Org. Chem. 1977, 42, 2645.
30. (d) Ogawa, A.; Miyake, J.; Karasaki, Y.; Murai, S.; Sonoda, N. J. Org. Chem. 1985, 50, 384.
31. (e) Ogawa, A.; Miyake, J.; Kambe, N.; Murai, S.; Sonoda, N. Bull. Chem. Soc. Jpn., 1985, 58, 1448.
32. (f) Shimada, K.; Hikage, S.; Takeishi, Y.; Takiakawa, Y. Chem. Lett. 1990, 1403.
33. (g) Takikawa, Y.; Watanabe, H.; Sasaki, R.; Shimada, K. Bull. Chem. Soc. Jpn. 1994, 67, 876.
34. (h) An, D.-L.; Toyota, K.; Yasunami, M.; Yoshifuji, M. Chem. Lett. 1995, 199.
35. Murai, T.; Hayashi, A.; Kanda, T.; Kato, S. Chem. Lett. 1993, 1469.
36. (a) Harirchian, B.; Magnus, P. J. Chem. Soc., Chem. Commun., 1977, 522.
37. (b) Lemarié, M.; Vallée, Y.; Worrell, M. Tetrahedron Lett. 1992, 33, 6131.
38. (c) Murai, T.; Takada, H.; Kanda, T.; Kato, S. Tetrahedron Lett. 1994, 35, 8817.
39. For reviews, see: (a) Luh, L.-Y.; Ni, Z.-J. Synthesis, 1990, 89.
40. (b) Kolb, M. Synthesis, 1990, 171.
41. (a) Jensen, K.; Henriksen, L. Acta Chem. Scand. 1970, 24, 3213.
42. (b) Gronowitz, S.; Frejd, T. Acta Chem. Scand. 1973, 27, 2242.
43. (c) Gröbel, B. -T.; Seeback, D. Chem. Ber. 1977, 110, 852.
44. (d) Denis, J. N.; Krief, A. Tetrahedron Lett. 1982, 23, 3407.
45. (e) Denis, J. N.; Krief, A. Tetrahedron Lett. 1982, 23, 3411.
46. (f) Stang, P. J.; Roberts, K. A.; Lynch, L. E. J. Org. Chem. 1984, 49, 1653.
47. Eliel, E. L.; Wilen, S. H.; Mander, L. N. in Stereochemistry of Organic Compounds, John Wiley & Sons Inc.: New York. 1994 p 539.
48. (a) Vallée, Y.; Worrell, M. J. Chem. Soc., Chem. Commun. 1992, 1680.
49. (b) Shimada, K.; Oikawa, S.; Nakamura, H.; Takikawa, Y. Chem. Lett. 1995, 135.
50. (c) Murai, T.; Takada, H.; Kanda, T.; Kato, S. Chem. Lett. 1995, 1057.
51. The instability of α-monosubstituted selenothioesters 6 was in sharp contrast to that of α-disubstituted esters 7. For example, during the purification of 6 (R = cyclohexenyl, R′ = n-Bu) through silica gel column, the deep purple color of 6 gradually turned yellow to give a complex mixture, whereas ester 7c could be stored in the refrigerator at least for one month.
52. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.