TADDOL-TICL2 CATALYZED DIELS-ALDER REACTIONS - UNEXPECTED INFLUENCE OF THE SUBSTITUENTS IN THE 2-POSITION OF THE DIOXOLANE RING ON THE STEREOSELECTIVITY

Authors
ALTAVA B BURGUETE MI FRAILE JM GARCIA JI LUIS SV MAYORAL JA ANA JRB VINCENT MJ
Citation
B. Altava et al., TADDOL-TICL2 CATALYZED DIELS-ALDER REACTIONS - UNEXPECTED INFLUENCE OF THE SUBSTITUENTS IN THE 2-POSITION OF THE DIOXOLANE RING ON THE STEREOSELECTIVITY, Tetrahedron : asymmetry, 8(15), 1997, pp. 2561-2570
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
15
Year of publication
1997
Pages
2561 - 2570
Database
ISI
SICI code
0957-4166(1997)8:15<2561:TCDR-U>2.0.ZU;2-P
Abstract
Several (3,5-dimethylphenyl)-1,3-dioxolane-4,5-demethanols have been s ynthesized, and their TiCl2 derivatives used as catalysts in the react ion of cyclopentadiene with (E)-2-butenoyl-1,3-oxazolidin-2-one. The s ubstituents in the 2-position of the dioxolane ring exert a decisive i nfluence on the extent and direction of the asymmetric induction and, consequently any possible enantiomer of the cycloadducts can be prefer entially obtained by changing these substituents. Molecular mechanics calculations of the structures and relative energies of the possible d ienophile-catalyst complexes offer a tentative explanation for the res ults described. (C) 1997 Elsevier Science Ltd.