Highly stereo and chemoselective iron-catalyzed alkenylation of organomagnesium compounds

Synthesis

Volumn , Issue 8, 1998, Pages 1199-1205

  Cahiez, Gérard ^a   Avedissian, Hovsep ^a  

^a Allée du Réseau Jean Marie Buckmaster   (France)

Author keywords

Alkenyl halides; Alkenylation; Cross coupling reaction; Iron; Organomagnesium compounds; Z or E alkenes

Indexed keywords

ALKENE DERIVATIVE; HALIDE; IRON; MAGNESIUM DERIVATIVE; ORGANOMAGNESIUM COMPOUND; UNCLASSIFIED DRUG;

CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN; SHORT SURVEY; STEREOCHEMISTRY;

EID: 0031871453     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2135     Document Type: Short Survey

References (36)

1. (a) Cahiez, G.; Marquais, S. Pure & Appl. Chem. 1996, 68, 669.
2. (b) Cahiez, G.; Marquais, S. Tetrahedron Lett. 1996, 37, 1773.
3. (a) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487.
4. (b) Tamura, M.; Kochi, J. K. Synthesis 1971, 93, 303.
5. (c) Tamura, M.; Kochi, J. K. J. Organomet. Chem. 1971, 31, 289.
6. (d) Tamura, M.; Kochi, J. K. Bull. Chem. Soc. Jpn. 1971, 44, 3063.
7. (e) Tamura, M.; Kochi, J. K. Synthesis 1971, 303.
8. (f) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351.
9. (g) Neuman, S.; Kochi, J. K. J. Org. Chem. 1975, 40, 599.
10. (h) Smith, R. S.; Kochi, J. K. J. Org. Chem. 1976, 41, 502.
11. See also: Molander, G.; Rahn, B.; Shubert, D. C.; Bonde, S. E. Tetrahedron Lett. 1983, 24, 5449.
12. For some examples of cross-coupling reactions from enol phosphates, see: (a) Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915.
13. (b) Takai, K.; Oshima, K.; Nazaki, H. Tetrahedron Lett. 1980, 21, 2531.
14. (c) Takai, K.; Oshima, K.; Nazaki, H. Bull. Chem. Soc. Jpn. 1984, 57, 108.
15. (d) Sum, F.-W. ; Weiler, L. Can. J. Chem. 1979, 57, 1431.
16. (e) Nicolaou, K. C.; Shi, G.-Q.; Gunzner, J. L.; Gärtner, P.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 5467.
17. (f) Sato, M.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1609.
18. (g) Blaszczak, L.; Winkler, J.; Kuhn, S. O. Tetrahedron Lett. 1976, 17, 4405.
19. Welch, S.; Walters, M. E. J. Org. Chem. 1978, 43, 2715.
20. (a) Kumada, M. Pure Appl. Chem. 1980, 52, 669.
21. (b) Tamao, K.; Kumada, M. In The Chemistry of the Metal-Carbon Bond; Hartley, Ed.; Wiley: New York, 1987; Chap. 4, p 819.
22. (c) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
23. (d) Erdik, E. Tetrahedron 1992, 48, 9577.
24. (e) Knochel, P.; Singer, R.D. Chem. Rev. 1993, 93, 2117.
25. (f) Stille, J.K. Angew. Chem. 1986, 98, 505.
26. (g) Kalini, V.N. Synthesis 1992, 413.
27. (h) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749.
28. (a) Normant, J. F.; Cahiez, G.; Chuit, C.; Villieras, J. J. Organomet. Chem. 1974, 77, 269.
29. (b) Alexakis, A.; Cahiez, G.; Normant, J. F. Org. Synth. Coll. Vol. VII 1990, 290.
30. (a) Zweifel, G.; Whitney, C. J. Am. Chem. Soc. 1967, 2753.
31. (b) Zweifel, G.; Miller, J. A. Org. React. 1984, 32, 375.
32. Commerçon, A.; Normant, J.; Villieras, J. J. Organomet. Chem. 1975, 93, 415.
33. Cousseau, J. Synthesis 1980, 805.
34. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Vskokovic, M. R. Tetrahedron Lett. 1992, 33, 917.
35. Mewshaw, R. E. Tetrahedron Lett. 1989, 30, 3753.
36. Wamhoff, E.W.: Martin, D.G.; Johnson, W.S. Org. Synth. Coll. Vol. IV, 1963, 162.