Abstract
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.
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