Design of optically active selenium reagents having a chiral tertiary amino group and their application to asymmetric inter- and intramolecular oxyselenenylations

Tetrahedron

Volumn 53, Issue 6, 1997, Pages 2029-2048

  Fujita, Ken ichi ^a   Murata, Kazuhisa ^a   Iwaoka, Michio ^b   Tomoda, Shuji ^b  

^a NATL INST OF MAT AND CHEM RES   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; SELENIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0031562120     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01166-0     Document Type: Article

References (46)

1. 1. a) Organoselenium Chemistry; Liotta, D. Ed.; Wiley: London, 1987.
2. b) Selenium Reagents and Intermediates in Organic Synthesis; Paulmier, C. Ed.; Pergamon Press: Oxford, 1986.
3. c) Schmid, G. H.; Garratt, D. G. In The Chemistry of Double-Bonded Functional Groups; Patai, S. Ed., Wiley: London, 1977; Supp. A, Part 2.
4. d) Garratt, D. G.; Kabo, A. Can. J. Chem. 1980, 58, 1030-1041.
5. e) Reich, H. J. J. Org. Chem., 1974, 39, 428-429.
6. f) Gassman, P. G.; Miura, A.; Miura, T. J. Org. Chem., 1982, 47, 951-954.
7. g) Tomoda, S.; Takeuchi, Y.; Nomura, Y. Tetrahedron Lett., 1982, 23, 1361-1364.
8. h) Tomoda, S.; Takeuchi, Y.; Nomura, Y. J. Chem. Soc., Chem. Commun., 1982, 871-872.
9. i) Tomoda, S.; Takeuchi, Y.; Nomura, Y. Chem. Lett., 1982, 1733-1734.
10. j) Hayama, T.; Tomoda, S.; Takeuchi, Y.; Nomura, Y. Tetrahedron Lett., 1982, 23, 4733-4734.
11. 2. a) Clive, D. J.; Chittattu, G.; Curtis, N. J.; Kiel, W. A.; Wong, C. K. J. Chem. Soc., Chem. Commun., 1977, 725-727.
12. b) Goldsmith, D.; Liotta, D.; Lee, C.; Zima, G. Tetrahedron Lett., 1979, 50, 4801-4804.
13. c) Nicolaou, K. C.; Seitz, S. P.; Sipio, W. J.; Blount, J. F. J. Am. Chem. Soc., 1979, 101, 3884-3893.
14. d) Nicolaou, K. C.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc., 1980, 102, 3784-3793.
15. 3. Tomoda, S.; Iwaoka, M. In Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed.; John Wiley & Sons: Chichester, 1995.
16. 4. Sharpless, K. B.; Lauer, R. F. J. Org. Chem., 1974, 39, 429-430.
17. 5. Tomoda, S.; Iwaoka, M. Chem. Lett., 1988, 1895-1898.
18. 6. Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. Heteroatom Chem., 1995, 5, 247-257.
19. 7. Fujita, K.; Iwaoka, M.; Tomoda, S. Chem. Lett., 1992, 1123-1124.
20. 8. Tomoda, S.; Fujita, K.; Iwaoka, M. J. Chem. Soc., Chem. Commun., 1990, 129-131.
21. 9. Tomoda, S.; Fujita, K.; Iwaoka, M. Phosphorus, Sulfur, and Silicon, and the Related Elements, 1992, 67, 125-130.
22. 10. Tomoda, S.; Usuki, Y.; Fujita, K.; Iwaoka, M. Rev. Heteroatom Chem., 1991, 4, 249-277.
23. 11. Noyori, R. Chem. Soc. Rev., 1989, 18, 187-208.
24. 12. Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett., 1994, 35, 9403-9406.
25. 13. Fujita, K.; Iwaoka, M.; Tomoda, S. Chem. Lett., 1994, 923-926.
26. 14. a) Deziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem., 1993, 58, 3619-3621.
27. b) Deziel, R.; Malenfant, E.; Belanger, G. J. Org. Chem. 1996, 61, 1875-1876.
28. 15. Wirth, T. Angew. Chem. Int. Ed. Engl., 1995, 34, 1726-1728.
29. 16. Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc., 1996, 118, 8077-8084.
30. 17. a) Baiwir, P. M.; Llabres, G.; Dideberg, O.; Dupont, L.; Piette, J. L. Acta Crystallogr. 1975, B31, 2188-2191.
31. b) Tomoda, S.; Iwaoka, M. J. Chem. Soc., Chem. Commun., 1990, 231-233.
32. c) Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc., 1990, 112, 8265-8268.
33. d) Burling, F. T.; Goldstein, B. M. Am. Chem. Soc., 1992, 114, 2313-2320.
34. e) Barton, D. H. R.; Hall, M. B.; Lin, Z.; Parekh, S. I.; Reibenspies, J. Am. Chem. Soc., 1993, 115, 5056-5059.
35. 18. Iwaoka, M.; Tomoda, S. Phosphorus, Sulfur, and Silicon, and the Related Elements, 1992, 67, 125-128.
36. 19. Iwaoka, M.; Tomoda, S. J. Org. Chem., 1995, 60, 5299-5302.
37. 20. a) Shing, T. K. M. Tetrahedron, 1988, 44, 7261-7264.
38. b) Masaki, Y.; Oda, H.; Kazuta, K.; Usui, A.; Itoh, A.; Xu, F. Tetrahedron Lett., 1992, 33, 5089-5092.
39. 21. Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. Tetrahedron Lett., 1995, 36, 5219-5222.
40. 22.a) Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroder, G.; Sharpless, K. B. J. Am. Chem. Soc., 1988, 110, 1968-1970.
41. b) Groves, J. T.; Viski, P. J. Org. Chem., 1990, 55, 3628-3634.
42. 23. Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun., 1995, 1641-1642.
43. 24. Albinati, A.; Bravo, P.; Ganazzoli, F.; Resnati, G.; Viani, F. J. Chem. Soc. Perkin Trans. I, 1986, 1405-1415.
44. 25. a) Maigrot, N.; Mazaleyrat, J.-P. Synthesis, 1985, 317-320.
45. b) Hawkins, J. M.; Fu, G. C. J. Org. Chem., 1986, 51, 2820-2822.
46. 26. Marzi, M.; Misiti, D. Tetrahedron Lett., 1989, 30, 6075-6076.