Ligand-Controlled Palladium-Catalyzed Asymmetric [4+3] and [2+3] Annulation Reactions of Spirovinylcyclopropyl Oxindoles with o-Quinone Methides.

Abstract

We herein report regiodivergent ligand-controlled palladium-catalyzed asymmetric cycloaddition reactions between spirovinylcyclopropyl oxindoles and o-quinone methides. Specifically, by using the chiral P,P-ligand Segphos (L5), we obtained various spirooxindole-3,4-benzo[b]oxepanes in moderate to good yields with excellent enantioselectivities via [4+3] cycloaddition reactions. In contrast, reactions involving Trost's ligand (L7) showed different regio- and stereoselectivities, affording bispirooxindole heterocyclic compounds in good yields via [2+3] cycloaddition reactions.