Unprecedented Barbier-type reactions catalysed by titanocene(III)

Chemical Communications

Volumn , Issue 22, 2004, Pages 2628-2629

  Rosales, Antonio ^a   Oller López, Juan L ^a   Justicia, José ^a   Gansäuer, Andreas ^b   Oltra, J Enrique ^a   Cuerva, Juan M ^a  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE; TITANOCENE;

ALLYLATION; ARTICLE; BENZYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; OPTICAL DENSITY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 9944256489     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b411173g     Document Type: Article

References (19)

1. Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 1 and 2.
2. M. T. Reetz, in Organometallics in Synthesis. A manual, ed. M. Schlossers, John Wiley & Sons, Chichester, England, 2002, pp. 817-923.
3. (a) Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207;
4. (b) F. Sato, H. Urabe and S. Okamoto, Chem. Rev., 2000, 100, 2835.
5. (a) R. O. Duthaler and A. Hafner, Chem. Rev., 1992, 92, 807;
6. (b) A. H. Hoveyda and J. P. Morken, Angew. Chem., Int. Ed Engl., 1996, 35, 1263;
7. S. E. Denmark and J. Fu, Chem. Rev., 2003, 103, 2763.
8. (a) A. F. Barrero, A. Resales, J. M. Cuerva and J. E. Oltra, Org. Lett, 2003, 5, 1935;
9. (b) J. Justicia, A. Rosales, E. Buñuel, J. L. Oller-López, M. Valdivia, A. Haïdour, J. E. Oltra, A. F. Barrero, D. J. Cárdenas and J. M. Cuerva, Chem. Eur. J., 2004, 10, 1778.
10. 4) and the solvent removed. The residue was chromatographed (hexane-EtOAc, 4:1) to give 1-tridecen-4-ol (114 mg, 90%). For an alternative protocol to be used with unsaturated substrates see ESI.
11. (a) A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745;
12. (b) H. B. Kagan, Tetrahedron, 2003, 59, 10351.
13. For example, the high reactivity of samarium diiodide does not allow the allylation of aromatic carbonyl compounds because they undergo pinacol coupling instead (see ref. 7). For other problems related to aliphatic aldehydes see: J. Souppe, J. L. Namy and H. B. Kagan, Tetrahedron Lett., 1982, 23, 3497.
14. M. Newcomb, in Radicals in Organic Synthesis, ed. P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim, Germany, 2001, vol. 1, pp. 317-336.
15. The relevant idea about a titanium(III)-bound carbonyl group acting as a "radical trap" for the allyl radical was suggested by a referee.
16. A. Fürstner, Chem. Rev., 1999, 99, 991.
17. R. Noyori, Angew. Chem., Int. Ed., 2002, 41, 2008.
18. A. Gansäuer, H. Bluhm, B. Rinker, S. Narayan, M. Schick, T. Lauterbach and M. Pierobon, Chem. Eur. J., 2003, 9, 531.
19. H. Urabe, K. Yoshikawa and F. Sato, Tetrahedron Lett., 1995, 36, 5595.