The aldol-Grob reaction: Regioselective synthesis of (E)-alkenes from aldehydes and ketones with ytterbium triflate catalysis

European Journal of Organic Chemistry

Volumn , Issue 9, 2003, Pages 1631-1634

  Curini, Massimo ^a   Epifano, Francesco ^a   Maltese, Federica ^a   Marcotullio, Maria Carla ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Aldehydes; Alkenes; Ketones; Lanthanides

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; KETONE DERIVATIVE; LANTHANIDE; LEWIS ACID; TRIFLUOROMETHANESULFONIC ACID; YTTERBIUM;

ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 0038666326     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300076     Document Type: Article

References (28)

1. [1a] R. Kane, Ann. Physik Chem. 1838, 44, 475; J. Prakt. Chem. 1838, 15, 129.
2. [1a] R. Kane, Ann. Physik Chem. 1838, 44, 475; J. Prakt. Chem. 1838, 15, 129.
3. [1b] A. Wurtz, Bull. Soc. Chim. Fr. 1872, 17, 436; Ber. 1872, 5, 326.
4. [1b] A. Wurtz, Bull. Soc. Chim. Fr. 1872, 17, 436; Ber. 1872, 5, 326.
5. [1c] A. T. Nielsen, W. J. Houlihan, Org. React. 1968, 16.
6. C. A. Grob, Angew. Chem. Int. Ed. Engl. 1969, 8, 535.
7. X. L. Armesto, M. Canle, M. Losada, J. Santaballa, J. Org. Chem. 1994, 59, 4659.
8. M. De Giacomo, R. M. Bettolo, R. Scarpelli, Tetrahedron Lett. 1997, 38, 3469.
9. [5a] A. Nagumo, A. Matsukuma, F. Inoue, T. Yamamoto, H. Suemune, K. Sakai, Chem. Commun. 1990, 1538.
10. [5b] H. Yamamoto, H. Suemune, K. Sakai, Tetrahedron 1991, 47, 8523.
11. [6a] C. M. Amann, P. V. Fisher, M. L. Pugh, F. G. West, J. Org. Chem. 1998, 63, 2806.
12. [6b] G. A. Molander, Y. Le Huerou, G. A. Brown, J. Org. Chem. 2001, 66, 4511.
13. [7a] A. Waldemar, L. Blancafort, J. Org. Chem. 1997, 62, 1623.
14. [7b] T. Koch, K. Bandemer, W. Boland, Helv. Chim. Acta 1997, 80, 838.
15. [7c] D. Renneberg, H. Pfander, C. J. Leumann, J. Org. Chem. 2000, 65, 9069.
16. J. J. Grove, C. W. Holzhapfel, D. B. G. Williams, Tetrahedron Lett. 1996, 37, 5817.
17. S. Nagumo, A. Matsukuma, H. Suemune, K. Sakai, Tetrahedron 1993, 49, 10501.
18. [10a] G. W. Kabalka, D. Tejedor, N. S. Li, R. R. Malladi, S. Trotman, J. Org. Chem. 1998, 63, 6438.
19. [10b] G. W. Kabalka, D. Tejedor, N. S. Li, R. R. Malladi, S. Trotman, Tetrahedron 1998, 54, 15525.
20. [10c] G. W. Kabalka, N. S. Li, D. Tejedor, R. R. Malladi, X. Gao, S. Trotman, Synth. Commun. 1999, 29, 2783.
21. [10d] G. W. Kabalka, D. Tejedor, N. S. Li, R. R. Malladi, S. Trotman, J. Org. Chem. 1999, 64, 3157.
22. G. M. Strunz, H. Finlay, Phytochemistry 1995, 39, 731.
23. G. M. Strunz, H. Finlay, Tetrahedron 1994, 50, 11113.
24. S. Kobayshi, M. Sugiura, H. Kitagawa, W. W. L. Lam, Chem. Rev. 2002, 102, 2227.
25. [14a] M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati, Tetrahedron Lett. 2001, 42, 3193.
26. [14b] M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati, Heterocycles 2001, 55, 1599.
27. [14c] M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati, Eur. J. Org. Chem. 2002, 1562.
28. [14d] M. Curini, F. Epifano, F. Maltese, O. Rosati, Tetrahedron Lett. 2002, 43, 4895.