First catalytic allyltitanation reactions

Chemical Communications

Volumn , Issue 6, 2005, Pages 775-777

  Bareille, Laurianne ^a   Le Gendre, Pierre ^a   Moïse, Claude ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; TITANOCENE;

ARTICLE; CATALYSIS; CATALYTIC ALLYLTITANATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 14644405598     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b414322a     Document Type: Article

References (24)

1. (a) F. Sato, S. Ijima and M. Sato, Tetrahedron Lett., 1981, 22, 243;
2. (b) B. Klei, J. H. Teuben and H. de Liefde Meijer, J. Chem. Soc., Chem. Commun., 1981, 342.
3. (a) S. Collins, W. P. Dean and D. G. Ward, Organometallics, 1988, 7, 2289;
4. (b) J. Szymoniak, H. Lefranc, J. Besançon and C. Möise, Synthesis, 1995, 815;
5. (c) H. Urabe, K. Yoshikawa and F. Sato, Tetrahedron Lett., 1995, 31, 5595;
6. (d) J. Szymoniak, D. Felix, J. Besançon and C. Moïse, Tetrahedron, 1996, 52, 4377;
7. (e) N. Thery, J. Szymoniak and C. Möise, Eur. J. Org. Chem., 2000, 1483.
8. (a) A. Gansäuer, M. Pierobon and H. Bluhm, Angew. Chem., Int. Ed., 1998, 37, 101;
9. (b) A. Gansäuer and H. Bluhm, Chem. Commun., 1998, 2143.
10. For a titanium-catalysed reaction with similar concept see: A. Fürstner and A. Hupperts, J. Am. Chem. Soc., 1995, 117, 4468.
11. (a) F. Sato, T. Jinbo and M. Sato, Tetrahedron Lett., 1980, 21, 2171;
12. (b) R. Halterman, T. M. Ramsey and Z. L. Chen, J. Org. Chem., 1994, 59, 2642;
13. (c) P. Beagley, P. J. Davies, A. J. Blacker and C. White, Organometallics, 2002, 21, 5852;
14. (d) R. Shu, J. F. Harrod and A. M. Lebuis, Can. J. Chem., 2002, 80, 489.
15. (a) M. B. Carter, B. Schiøtt, A. Gutiérrez and S. L. Buchwald, J. Am. Chem. Soc., 1994, 116, 11667;
16. (b) K. J. Barr, S. C. Berk and S. L. Buchwald, J. Org. Chem., 1994, 59, 4323;
17. (c) X. Verdaguer, M. C. Hansen, S. C. Berk and S. L. Buchwald, J. Org. Chem., 1997, 62, 8522.
18. 3-1,2-dimethylallyl) at -20 °C led to the homoallylic alcohol 1 with a ratio of the two diastereoisomers (anti: syn) equal to 68: 32.
19. H. A. Martin and F. Jellinek, J. Organomet. Chem., 1968, 12, 149.
20. (a) C. T. Aitken, J. F. Harrod and E. Samuel, J. Am. Chem. Soc., 1986, 108, 4059;
21. (b) J. F. Harrod, Y. Mu and E. Samuel, Can. J. Chem., 1992, 70, 2980;
22. (c) E. Spaltenstein, P. Pilar, K. A. Kreutzer, C. A. Willoughby, W. M. Davis and S. L. Buchwald, J. Am. Chem. Soc., 1994, 116, 10308;
23. (d) F. Lunzer, C. Marschner and S. Landgraf, J. Organomet. Chem., 1998, 568, 1998.
24. S. C. Berk, K. A. Kreutzer and S. L. Buchwald, J. Am. Chem. Soc., 1991, 113, 5093.