An allylation-metathesis sequence as a convergent strategy towards enantiopure equivalents of highly functionalized cyclic dienes

Tetrahedron Letters

Volumn 44, Issue 38, 2003, Pages 7197-7199

  De Fays, Laurence ^a   Adam, Jean Michel ^b   Ghosez, Léon ^a  

^a INSTITUT EUROPÉEN DE CHIMIE ET BIOLOGIE   (France)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKADIENE; ALLYL COMPOUND; REAGENT; SILANE DERIVATIVE; TITANIUM DERIVATIVE;

ALLYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLIZATION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; RING CLOSING METATHESIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0041508444     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01791-X     Document Type: Article

References (15)

1. Adam J.-M., Ghosez L., Houk K.N. Angew. Chem., Int. Ed. 38:1999;2728-2730.
2. Fürstner A., Langemann K. J. Am. Chem. Soc. 119:1997;9130-9136.
3. Cossy J., Bauer D., Bellosta V. Tetrahedron Lett. 40:1999;4187-4188.
4. Scholl M., Grubbs R.H. Tetrahedron Lett. 40:1999;1425-1428.
5. Ahmed M., Barrett A.G.M., Beall J.C., Braddock D.C., Flack K., Gibson V.C., Procopriou P.A. Tetrahedron. 55:1999;3219-3232.
6. Mulzer J., Hanbauer M. Tetrahedron Lett. 41:2000;33-36.
7. Ramachandran P.V., Reddy M.R.V., Brown H.C. Tetrahedron Lett. 41:2000;583-586.
8. Felpin F.X., Girard S., Vo-Than G., Robins R.J., Villieras J., Lebreton J. J. Org. Chem. 66:2001;6305-6312.
9. Cossy J., Willis C., Bellosta V., Bouzbouz S. J. Org. Chem. 67:2002;1982-1992.
10. Heo J.-N., Micaizio G.C., Roush W.R. Org. Lett. 5:2003;1693-1696.
11. Heo J.-N., Holson E.B., Roush W.R. Org. Lett. 5:2003;1697-1700.
12. (a) Synthesis of 3-butenal: Crimmins, M. T.; Kirincich, S. T.; Wells, A. J.; Choy, A. L. Synth. Commun. 1998, 28, 3675-3679;
13. (b) Synthesis of 5-hexenal: Ikeda, T.; Yue, S.; Hutchinson, C. R. J. Org. Chem. 1985, 50, 5193-5199.
14. Hafner A., Duthaler R.O., Marti R., Rihs G., Rothe-Streit P., Schwarzenbach F. J. Am. Chem. Soc. 114:1992;2321-2336.
15. We thank Dr M. Laguerre for his help.