Diastereo‐ and Enantioselective Construction of Dihydroisocoumarin‐Based Spirooxindole Frameworks <i>via</i> Organocatalytic Tandem Reactions

Abstract

Abstract An organocatalytic asymmetric approach has been developed for the ennantioselective construction of dihydroisocoumarin‐based spirooxindole frameworks in high yields, excellent diastereo‐ and enantioselectivities (up to 99%, all &gt;95:5 dr , up to 99% ee ). This approach takes advantage of chiral thiourea‐tertiaryamine catalyzed tandem reaction of isatins with enolizable homophthalic anhydride, which has wide substrate scope and can be performed with low catalyst loading. This reaction not only provides an efficient and useful method for constructing enantioenriched dihydroisocoumarin‐based spirooxindole scaffold, but also will enrich the research contents of catalytic asymmetric tandem reactions and enantioselective synthesis of biologically important spirooxindoles. magnified image