145917-18-6Relevant articles and documents
The effect of Lewis acids on the intramolecular Diels-Alder reaction of the furan diene
Rogers, Christine,Keay, Brian A.
, p. 2929 - 2947 (2007/10/02)
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 deg 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 molpercent) provided a higher quantity of adduct than excess Lewis acid when the enone was substituted with alkyl groups.The scope was extended to include a precursor containing a five carbon atom side arm, and two examples containing acetylenic dienophiles that were activated by a carbonyl moiety on the side arm.Precursors having a four carbon atom side arm provided only oxatricyclo adducts having the side arm syn to the oxygen bridge.The assignment of the stereochemistry of the oxatricyclo adducts is discussed in detail.