Stereoselective 1,4-addition of Grignard reagents to chiral γ-alkoxy-α,β-unsaturated ketones

Tetrahedron Asymmetry

Volumn 8, Issue 22, 1997, Pages 3821-3828

  Raczko, Jerzy ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLBUTYRIC ACID DERIVATIVE; TYLOSIN DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030735265     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00520-X     Document Type: Article

References (43)

1. Reviews: (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev., 1992, 92, 771.
2. (b) Leonard, J. Contemp. Org. Synth., 1994, 1, 387.
3. (c) Yamamoto, Y. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1995: Vol. E 21b, 2041.
4. Kharasch, M. S.; Tawney, P. O. J. Am. Chem. Soc., 1941, 63, 2308.
5. (a) Roush, W. R.; Lesur, B. M. Tetrahedron Lett., 1983, 24, 2231;
6. (b) Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Chong, W. K. J. Am. Chem. Soc., 1987, 109, 7575;
7. (c) Roush, W. R.; Michaelides, M. R.; Tai, Lesur, B. M.; D. F.; Chong, W. K.; Harris, D. J. J. Am. Chem. Soc., 1989, 111, 2984.
8. (a) Yamamoto, Y.; Nishii, S.; Ibuka, T. J. Chem. Soc., Chem. Commun., 1987, 464;
9. (b) ibid., 1987, 1572;
10. (c) Yamamoto, Y.; Chounan, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc., 1992, 114, 7652.
11. (a) Leonard, J.; Ryan, G. Tetrahedron Lett., 1987, 28, 2525;
12. (b) Leonard, J.; Ryan, G.; Swain, P. A. Synlett, 1990, 613;
13. (c) Leonard, J.; Mohialdin, S.; Reed, D.; Jones, M. F. Synlett, 1992, 741;
14. (d) Leonard, J.; Mohialdin, S.; Reed, D.; Ryan, G.; Swain, P. A. Tetrahedron, 1995, 51, 12843.
15. Hanessian, S.; Sumi, K. Synthesis, 1991, 1083.
16. Salomon, R. G., Miller, D. B., Raychaudhuri, S. R., Avasthi, K., Lal, K., Levison, B. S. J. Am. Chem. Soc., 1984, 106, 8296.
17. Larchêveque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun., 1989, 31.
18. Nemoto, H.; Ando, M.; Fukumoto, H. Tetrahedron Lett., 1990, 31, 6205.
19. (a) Dondoni, A.; Merino, P.; Orduna, P. Tetrahedron Lett., 1991, 32, 3247;
20. (b) Dondoni, A.; Boscarato, A.; Marra, A. Synlett, 1993, 256.
21. (a) Reetz, M. T.; Ršhring, D. Angew. Chem., 1989, 101, 1732; Angew. Chem., Int. Ed. Engl., 1989, 28, 1706.
22. (a) Reetz, M. T.; Ršhring, D. Angew. Chem., 1989, 101, 1732; Angew. Chem., Int. Ed. Engl., 1989, 28, 1706.
23. (b) Iako, I.; Uiber, P.; Mann, A.; Taddei, M.; Wermuth, C.-G. Tetrahedron Lett., 1990, 31, 1011.
24. (a) Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J. Org. Chem., 1986, 51, 5041;
25. (b) ibid., 1988, 53, 1600;
26. (c) Bernardi, A.; Cardani, S.; Scolastico, C.; Villa, R. Tetrahedron, 1990, 46, 1987.
27. Yoda, H., Shirai, T., Katagiri, T., Takabe, K., Kimata, K., Hosoya, K. Chem. Lett. 1990, 2037.
28. Burgess, K., Cassidy, J., Henderson, I. J. Org. Chem., 1991, 56, 2050.
29. (a) Isobe, M.; Kitamura, M.; Goto, T. Tetrahedron Lett., 1979, 20, 3465;
30. (b) ibid., 1980, 21, 4772;
31. (c) Isobe, M.; Ichikawa, Y.; Funabashi, Y.; Mio, S.; Goto, T. Tetrahedron, 1986, 42, 2863.
32. (a) Alcaraz, C.; Carretero, J. C.; Dominguez, E. Tetrahedron Lett., 1991, 32, 1385;
33. (b) Dominguez, E.; Carretero, J. C. Tetrahedron Lett., 1993, 34, 5803;
34. (c) Carretero, J. C.; Dominguez, E. J. Org. Chem., 1993, 58, 1596.
35. (a) Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. J. Am. Chem. Soc., 1981, 103, 1224;
36. (b) ibid., 1982, 104, 2027;
37. (c) Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. Tetrahedron Lett., 1979, 20, 2327.
38. Ziegler, F. E.; Gilligan, P. J. J. Org. Chem., 1981, 46, 3874.
39. (a) Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, T. Tetrahedron Lett., 1986, 27, 4025;
40. (b) Matsuzawa, S.; Horiguchi, Y.; Nakamura, E.; Kuwajima, T. Tetrahedron , 1989, 45, 349.
41. Garvey, G. J.; Kimura, M. J. Org. Chem., 1982, 47, 1982.
42. (a) Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc., 1989, 111, 6524.
43. (b) Bernardi, A.; Capelli, A. M.; Gennari, C.; Scolastico, C. Tetrahedron: Asymmetry, 1990, 1, 21.