Canadian Journal of Chemistry

The effect of Lewis acids on the intramolecular Diels-Alder reaction of the furan diene

C Rogers, BA Keay

Index: Rogers, Christine; Keay, Brian A. Canadian Journal of Chemistry, 1992 , vol. 70, # 12 p. 2929 - 2947

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Citation Number: 48

Abstract

A general method is described for effecting the intramolecular Diels-Alder reaction of the furan diene in which the side arm connecting the diene to the dienophile contains four carbon atoms. The use of 1.1 equivalents of methylaluminum dichloride at-78° C for 2-8 h shifts the Diels-Alder equilibrium towards the products and provides the oxatricyclo adducts in good to excellent yield. Catalytic quantities of methylaluminum dichloride (10 mol%) ...