Hydrogenation of substituted aromatic aldehydes: Nucleophilic trapping of the reaction intermediate, application to the efficient synthesis of methylene linked flavanol dimers

Tetrahedron Letters

Volumn 46, Issue 31, 2005, Pages 5177-5180

  Boyer, François Didier ^a   Ducrot, Paul Henri ^a  

^a CEMAGREF   (France)

Author keywords

Catechin; Flavanol; Hydrogenation

Indexed keywords

ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; BENZALDEHYDE DERIVATIVE; CARBENE; DIMER; FLAVANOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HYDROGENATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 21344456722     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.132     Document Type: Article

References (21)

1. J. Wang, H. He, Y. Shen, and X. Hao Tetrahedron Lett. 46 2005 169 172
2. S. Kasai, S. Watanabe, J. Kawabata, S. Tahara, and J. Mizutani Phytochemistry 31 1992 787 790
3. T. Hatano, H. Miyatake, M. Natsume, N. Osakabe, T. Takizawa, H. Ito, and T. Yoshida Phytochemistry 59 2002 749 758
4. C. Saucier, I. Pianet, M. Laguerre, and Y. Glories J. Chim. Phys. Phys. Chim. Biol. 95 1998 357 365
5. D.F. Lee, E.E. Swinny, and G.P. Jones Tetrahedron Lett. 45 2004 1671 1674
6. P. Kiatgrajai, J.D. Wellons, L. Gollob, and J.D. White J. Org. Chem. 15 1982 2913 2917
7. N.E. Es-Safi, H. Fulcrand, V. Cheynier, and M. Moutounet J. Agric. Food. Chem. 47 1999 2096 2102
8. T. Escribano-Bailón, M. Álvarez-García, J.C. Rivas Gonzalo, F.J. Heredia, and C. Santos-Buelga J. Agric. Food Chem. 49 2001 1213 1217
9. C. Saucier, C. Guerra, I. Piannet, M. Laguerre, and Y. Glories Phytochemistry 46 1997 229 234
10. N.E. Es-Safi, H. Fulcrand, V. Cheynier, and M. Moutounet J. Agric. Food. Chem. 48 2000 5946 5954
11. N.E. Es-Safi, H. Fulcrand, V. Cheynier, and M. Moutounet J. Agric. Food. Chem. 47 1999 2088 2095
12. R.W. Hemingway, and G.W. McGraw J. Liq. Chromatogr. 1 1978 163 179
13. L.Y. Foo, and R.W. Hemingway J. Wood. Chem. Technol. 5 1985 135 158
14. J. White, and L.Y. Foo Tetrahedron Lett. 31 1990 2789 2792
15. E. Kiehlmann, E.C. Lathioor, and K.W. Lai Org. Prep. Proced. Int. 28 1996 185 192
16. Es-Safi, C.N.E. Le Guernevé, H. Fulcrand, V. Cheynier, and M. Moutounet J. Agric. Food. Chem. 47 1999 5211 5217
17. Es-Safi, C. Le Guernevé, V. Cheynier, and M. Moutounet J. Agric. Food. Chem. 48 2000 4233 4240
18. Es-Safi, C. Le Guernevé, V. Cheynier, and M. Moutounet Tetrahedron Lett. 41 2000 1917 1921
19. H. Fulcrand, V. Cheynier, J. Oszmianski, and M. Moutounet Phytochemistry 46 1997 223 227
20. F.D. Boyer, N.E. Es-safi, J. Beauhaire, C. Le Guernevé, and P.H. Ducrot Bioorg. Med. Chem. Lett. 15 2005 559 562
21. +) (100), 411 (10), 277 (80). Product ions [429]: 411, 303, 289, 277, 151.