Stereoselective preparation of functionalized alkenylmagnesium reagents via an iodine-magnesium exchange reaction

Journal of Organic Chemistry

Volumn 64, Issue 4, 1999, Pages 1080-1081

  Rottländer, Mario ^a   Boymond, Laure ^b   Cahiez, Gérard ^b   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b Ecole Superieure de Chimie Organique et Minerale   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IODINE; MAGNESIUM; MAGNESIUM DERIVATIVE;

ARTICLE; CHEMICAL BINDING; LOW TEMPERATURE; ORGANIC CHEMISTRY; STEREOCHEMISTRY;

EID: 0038055666     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981941l     Document Type: Article

References (30)

1. (a) Silverman, G. S.; Rakita, P. E., Eds. Handbook of Grignard-Reagents; Marcel Dekker: 1996.
2. For recent applications, see: (b) Klos, A. M.; Heintzelman, G. R.; Weinreb, S. M. J. Org. Chem. 1997, 62, 3758.
3. (c) Taber, D. F.; Green, J. H.; Geremia, J. M. J. Org. Chem. 1997, 62, 9342.
4. (d) Hayashi, Y.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1998, 39, 63.
5. (e) Heron, N. M.; Adams, J. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 6205.
6. (f) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943.
7. Rieke, R. D.; Xiong, H. J. Org. Chem. 1991, 56, 3109.
8. Burns, T. P.; Rieke, R. D. J. Org. Chem. 1987, 52, 3674.
9. Boymond, L.; Rottländer, M.; Cahiez, G.; Knochel, P. Angew. Chem. 1998, 110, 1801; Angew. Chem., Int. Ed. Engl. 1998, 37, 1701.
10. Boymond, L.; Rottländer, M.; Cahiez, G.; Knochel, P. Angew. Chem. 1998, 110, 1801; Angew. Chem., Int. Ed. Engl. 1998, 37, 1701.
11. For a few examples of halogen-magnesium exchange reactions: (a) Villieras, J. Bull. Soc. Chim. Fr. 1967, 1520.
12. (b) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279.
13. (b) Paradies, H. H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem., Int. Ed. Engl. 1969, 8, 279.
14. (c) Smith, C. F.; Moore, G. J.; Tamborski, C. J. Organomet Chem. 1971, 33, C21.
15. (d) Cahiez, G.; Bernard, D.; Normant, J. F. J. Organomet. Chem. 1976, 113, 107.
16. (e) Seyferth, D.; Lambert, R. L. J. Organomet. Chem. 1973, 54, 1234.
17. (f) Redwane, N.; Moreau, P.; Commeyras, A. J. Fluorine Chem. 1982, 20, 699.
18. (g) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845.
19. (h) Nishiyama, H.; Isaka, K.; Itoh, K.; Ohno, K.; Nagase, H.; Matsumoto, K.; Yoshiwara, H. J. Org. Chem. 1992, 57, 407.
20. (i) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349.
21. Snieckus, V. Chem. Rev. 1990, 90, 879.
22. Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem. 1979, 168, 1.
23. The retention of the double bond is proven by the iodinolysis of the alkenylmagnesium reagent derived from the iodoallylic ether 1c, which gave exclusively the starting material back (>99% Z).
24. (a) Balkenhohl, F.; v. d. Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. 1996, 108, 2437; Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
25. (a) Balkenhohl, F.; v. d. Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. 1996, 108, 2437; Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
26. (b) Früchtel, J. S.; Jung, G. Angew. Chem. 1996, 108, 19; Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
27. (b) Früchtel, J. S.; Jung, G. Angew. Chem. 1996, 108, 19; Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
28. 3CN). Chemical yield 85% based on loading of the resin.
29. For theoretical studies on the origin of solvent acceleration in metalhalogen exchange reactions: Jedlicka, B.; Crabtree, R. H.; Siegbahn, P. E. M. Organometallics 1997, 16, 6021.
30. 2/ether 95:5), affording 3j (528 mg, 79% yield) as a colorless oil.