Synergistic catalysis of anthrone Diels-Alder reactions

[GRAPHICS] The combination of an amine base and Lewis acid (Li+) leads to synergistic catalysis of the Diels-Alder reaction of anthrone with methyl crotonate and some other less reactive dienophiles. These cycloadditions either do not occur with the individual catalysts used separately or they are greatly accelerated by the combined catalysts. DMSO solvent allows the use of LiCl as the Lewis acid source and can provide greater control of subsequent conversion to Michael adduct.