Title of article
Dynamic solvation effects on the endo/exo selectivity of the Diels–Alder reaction
Author/Authors
Cainelli، نويسنده , , Gianfranco and Galletti، نويسنده , , Paola and Giacomini، نويسنده , , Daria and Quintavalla، نويسنده , , Arianna، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2003
Pages
4
From page
93
To page
96
Abstract
The endo/exo stereoselectivity of the Diels–Alder cycloaddition between cyclopentadiene and 3-crotonoyl-2-oxazolidinone catalysed by Et2AlCl is temperature- and solvent-dependent. Eyring plots of ln(endo/exo) versus 1/T show different inversion temperatures (Tinv) depending on the reaction solvent. Using toluene-d8 we found a break temperature (TNMR) in a variable temperature 13C NMR experiment of the starting oxazolidinone, and this TNMR corresponded to the Tinv. In several cases the differential activation entropy manages the observed stereoselectivity.
Journal title
Tetrahedron Letters
Serial Year
2003
Journal title
Tetrahedron Letters
Record number
1659868
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