Allylation of carbonyl compounds in the presence of catalytic electrogenerated zinc. Unusual regioselectivity with a trifluorinated analog of prenyl bromide

Tetrahedron

Volumn 53, Issue 17, 1997, Pages 6027-6034

  Gosmini, C ^a   Rollin, Y ^a   Perichon, J ^a   Wakselman, C ^b   Tordeux, M ^b   Marival, L ^b  

^a CNRS   (France)

^b LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ELECTROCHEMISTRY; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030900981     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00280-9     Document Type: Article

References (20)

1. Yamamoto, Y. Acc. Chem. Res. 1987, 20, 2432.
2. Yamamoto, Y. Chem. Rev. 1993, 93, 2207-2293.
3. Blomberg, C.; "The Barbier reaction and related one-step processes", Springer-Verlag ed., Berlin, 1993.
4. (a) Hauser, R. C. and Breslow, O. S. Organic Synthesis, Col, Vol. III, J. Wiley and Sons. Inc., New York, 1955, p.408.
5. (b) Rieke, R. D.; Li, P. T. J.; Burns, T.P. and Uhm, S. T. J. Org. Chem. 1981, 46 , 4323.
6. (c) Boldrini, P.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1983, 48, 4108.
7. (d) Boudjouck, P.; Thompson, D. P.; Ohrbohm, W. H.; Han, B. H. Organometallics 1986, 5 , 1257.
8. (e) Santaniello, E.; Manzocchi, A. Synthesis 1977, 698.
9. (f) Bortolussi, N.; Seyden-Penne, J. Synth. Commun. 1989, 19, 2355.
10. (a) Rollin, Y.; Gebehenne, C; Derien, S.; Dunach, E. and Périchon, J. J. Organomet. Chem. 1993, 461, 9-13.
11. (b) Zylber, N.; Zylber, J.; Rollin, Y.; Dunach, E. and Périchon, J. J. Organomet. Chem. 1993, 444, 1-4.
12. (c) Gosmini, C.; Rollin, Y.; Gebehenne, C.; Lojou, E.; Ratovelomanana, V. and Perichon, J. Tetrahedron Lett. 1994, 35, 5637-5640.
13. (d) Rollin, Y.; Derien, S.; Dunach, E. Gebehenne, C. and Perichon, J. Tetrahedron 1993, 49, 7723 .
14. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198.
15. Martin, V.; Molines, H.; Wakselman, C. J. Fluorine Chem. 1993, 62 , 63.
16. Ruppert, J.F.; White, J.D. J. Org. Chem. 1976, 41 , 550.
17. We thank Martin V. for this experiment.
18. Troupel, M.; Rollin, Y.; Sock, O.; Meyer, G. and Perichon, J. Nouv. J. Chim. 1986, 11, 593.
19. Huang, Y.Z.; Zhang, L.J.; Chen, C. and Guo, G.Z. J. Organomet. Chem. 1991, 472, 47-52.
20. Brinkmann, H.; Hoffmann, R.W. Chem. Ber. 1990, 123(12), 2395-40.