Stereoselective Palladium-Catalyzed Arylation of Exo-Glycals with Aryl Iodides

Abstract

A novel methodology for the arylation of exo-glycals has been developed. A range of exo-glycals underwent reactions with aryl iodides in the presence of a palladium catalyst. The transformation proceeded in a stereoselective manner to afford Z-isomers. The developed transformation demonstrated excellent functional group tolerance.

Skeletal Transformations of Terpenoid Forskolin Employing an Oxidative Rearrangement Strategy

“…Therefore, we turned to a novel Pd(OAc) 2 -and AgOAc-catalyzed Heck-like reaction. 42 With this condition, the derivatives 2a−c of compound 2 were successfully prepared in 24−63% yields. The E configuration of the double bond was determined by the steric hindrance of the groups attached to both sides of the double bond and judged by the coupling constant.…”

“…Standard Heck reaction conditions are not suitable for compound 2 because it is sensitive to alkaline conditions. Therefore, we turned to a novel Pd­(OAc) 2 - and AgOAc-catalyzed Heck-like reaction . With this condition, the derivatives 2a – c of compound 2 were successfully prepared in 24–63% yields.…”

Synthesis of C,N-Glycosides via Brønsted Acid-Catalyzed Azidation of exo-Glycals

“…Recently, we developed a palladium-catalyzed arylation of exo-glycals. 30 Here, we report a practical Brønsted acid-catalyzed methodology for the synthesis of C,N-glycosides from exo-glycals.…”

“…Our research program is aimed at the derivatization of exo -glycals and their conversion to C-, C,N-, and C,C-glycosides. Recently, we developed a palladium-catalyzed arylation of exo -glycals . Here, we report a practical Brønsted acid-catalyzed methodology for the synthesis of C,N-glycosides from exo -glycals.…”