N-Heterocyclic Carbene Catalyzed Reaction of Phthalaldehydes: Controllable Stereoselective Synthesis of Polyhydroxylated Spiro- and Fused Indenones Dictated by the Structure of NHC Catalysts

Abstract

The N-heterocyclic carbene catalyzed stereoselective dimerization reactions of phthalaldehydes produced polyhydroxylated spiro- or fused indenones. The reaction pathways were dictated by the structures of NHC catalysts. Under the catalysis of a imidazole carbene, phthalaldehydes produced dihydroxylspiro[indene-2,1'-isobenzofuran]-3-ones in good to excellent yields, whereas a triazole carbene catalyzed reaction of phthalaldehydes afforded fully cis-trihydroxylindeno[2,1-a]inden-5-ones in high yields. This work not only provides a highly efficient method for the construction of valuable polyhydroxyl substituted indene derivatives that are not easily assembled by other synthetic means but also reflects the versatility of organocatalysis using N-heterocyclic carbenes.