Dynamic solvation effects on the endo/exo selectivity of the Diels-Alder reaction

Tetrahedron Letters

Volumn 44, Issue 1, 2003, Pages 93-96

  Cainelli, Gianfranco ^a   Galletti, Paola ^a   Giacomini, Daria ^a   Quintavalla, Arianna ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; SOLVENT; TOLUENE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLOADDITION; DIELS ALDER REACTION; ENTROPY; SOLVATION; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0037213008     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02477-2     Document Type: Article

References (19)

1. Oppolzer W. Trost B.M., Fleming I., Paquette L.A. Comprehensive Organic Synthesis. 5:1991;315 Pergamon Press, New York.
2. Nicolaou K.C., Snyder S.A., Montagnon T., Vassilikogiannakis G. Angew. Chem., Int. Ed. 41:2002;1668.
3. Corey E.J. Angew. Chem., Int. Ed. 41:2002;1650.
4. For a review, see: Cativiela C., Garcia J.I., Mayoral J.A., Salvatella L. Chem. Soc. Rev. 1996;209.
5. Glasstone, S.; Laidler, K. J.; Eyring, H. The Theory of Rate Processes; McGraw-Hill: New York, 1941; Chapter 4.
6. Buschmann H., Scharf H.-D., Hoffmann N., Esser P. Angew. Chem., Int. Ed. Engl. 30:1991;477.
7. Cainelli G., Giacomini D., Galletti P. Chem. Commun. 1999;567.
8. Cainelli, G.; Giacomini, D.; Galletti, P.; Orioli, P. Angew. Chem. 2000, 112, 533; Angew. Chem., Int. Ed. 2000, 39, 523.
9. Cainelli, G.; Giacomini, D.; Galletti, P.; Orioli, P. Angew. Chem. 2000, 112, 533; Angew. Chem., Int. Ed. 2000, 39, 523.
10. Cainelli G., Giacomini D., Galletti P., Orioli P., Paradisi F. Eur. J. Org. Chem. 1999;61.
11. Cainelli G., Giacomini D., Galletti P. Eur. J. Org. Chem. 1999;61.
12. Cainelli G., De Matteis V., Galletti P., Giacomini D., Orioli P. Chem. Commun. 2000;2351.
13. Cainelli G., Giacomini D., Galletti P., Marini A. Angew. Chem., Int. Ed. Engl. 35:1996;2849.
14. Cainelli G., Galletti P., Giacomini D., Orioli P. Tetrahedron Lett. 42:2001;7383.
15. Cainelli G., Giacomini D., Galletti P., Orioli P. Eur. J. Org. Chem. 2001;4509.
16. Cainelli G., Galletti P., Giacomini D., Orioli P., Polidoro M.A., Righetti M.C. Helv. Chim. Acta. 83:2000;1951.
17. Compounds 3 and 4 are known products, see: Kobayashi S., Ishitani H., Hachiya I., Araki M. Tetrahedron. 50:1994;11632.
18. The average standard deviation for the endo/exo ratio was less than 1%. Error bars are omitted in Fig. 1 for clarity.
19. For entropy-driven stereoselectivity see Ref. 14 and referencees cited therein.