Abstract
Recent experimental studies (D.C. Bradock, J.M. Brown and P.J. Guiry, J. Chem. Soc., Chem. Commun., (1993) 1244) on the stereoselectivity of the Diels-Alder reaction of thionofumarate derivatives with cyclopentadiene show that the hard or soft character of the Lewis acid catalysts can play a very important role controlling the steric course of this type of cycloaddition. RHF/3-21G ∗ ab initio calculations allow one to obtain a qualitatively correct description of the stereochemical outcome of that reaction both in the thermal and in the (hard) Lewis acid-catalysed cases.
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