Ytterbium-Catalyzed Enantioselective Diels-Alder Reaction

Significance

A highly stereoselective Diels-Alder reaction with Danishefsky-type dienes and electron-deficient alkenes has been accomplished using an ytterbium-BINAMIDE catalytic complex. A variety of dienophile substituents are tolerated, although the reaction is sensitive to steric interactions between the dienophile substituent and the silyloxy portion of the diene. The cyclic enone can be converted into a nonaflate, which the authors have shown to be a competent substrate for a variety of palladium-catalyzed cross-coupling reactions.