Palladium-catalyzed and samarium-promoted coupling of stereochemically-biased allylic acetates with carbonyl compounds

Tetrahedron

Volumn 66, Issue 1, 2010, Pages 222-226

  Jacquet, Olivier ^a   Bergholz, Timm ^a   Magnier Bouvier, Caroline ^a   Mellah, Mohamed ^a   Guillot, Régis ^a   Fiaud, Jean Claude ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

Coupling; Homogeneous catalysis; Ketone allylation; Palladium; Samarium

Indexed keywords

ACETIC ACID DERIVATIVE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; SAMARIUM DIIODIDE;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; DIASTEREOISOMER; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 70749129848     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.104     Document Type: Article

References (21)

1. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207-2293
2. Denmark S.E., and Fu J. Chem. Rev. 103 (2003) 2763-2793
3. Tamaru Y. Palladium-catalyzed reactions of allyl and related derivatives with organoelectrophiles. In: Negishi E. (Ed). Handbook of organopalladium chemistry in organic synthesis Vol. 2 (2002), J. Wiley & Sons 1917-1943
4. Tabuchi T., Inanaga J., and Yamaguchi M. Tetrahedron Lett. 27 (1986) 1195-1196
5. Médégan S., Hélion F., and Namy J.-L. Eur. J. Org. Chem. (2005) 4715-4722
6. Tabuchi T., Inanaga J., and Yamaguchi M. Tetrahedron Lett. 27 (1986) 601-602
7. Hanamoto T., Sugino A., Kikukawa T., and Inanaga J. Bull. Soc. Chim. Fr. 134 (1997) 391-394
8. Fiaud J.-C., and Legros J.-Y. J. Org. Chem. 52 (1987) 1907-1911
9. Dvorak D., Stary I., and Kocovsky P. J. Am. Chem. Soc. 117 (1995) 6130-6131
10. Bartels B., Garcia-Yebra C., Rominger F., and Helmchen G. Eur. J. Inorg. Chem. (2002) 2569-2586
11. Araki S., Ho M., Ito H., and Butsugan Y. J. Organomet. Chem. 333 (1987) 329-335
12. Ujikawa O., Inanaga J., and Yamaguchi M. Tetrahedron Lett. 21 (1989) 2837-2840
13. Inanaga J., Sakai S., Handa Y., Yamaguchi M., and Yokoyama Y. Chem. Lett. (1991) 2117-2118
14. Kusuda K., Inanaga J., and Yamaguchi M. Tetrahedron Lett. 30 (1989) 2945-2948
15. Malapelle A., Abdallah Z., Doisneau G., and Beau J.-M. Angew. Chem., Int. Ed 43 (2006) 846-849
16. Weitgenant J.A., Mortison J.D., and Helquist P. Org. Lett. 7 (2005) 3609-3612
17. Girard P., Namy J.-L., and Kagan H.B. J. Am. Chem. Soc. 102 (1980) 2693-2698
18. Sheldrick G.M. SHELXS-97, Program for Crystal Structure Solution (1997), University of Göttingen, Göttingen, Germany
19. Sheldrick G.M. SHELXL-97, Program for the Refinement of Crystal Structures from Diffraction Data (1997), University of Göttingen, Göttingen, Germany
20. Farrugia L.J. J. Appl. Crystallogr. 32 (1999) 837-838
21. Flack H.D. Acta Crystallogr. A39 (1983) 876-881