Details

Autor(en) / Beteiligte

• Nakao, Shuichi
• Saikai, Miki
• Nishimoto, Yoshihiro
• Yasuda, Makoto

Titel

InBr3‐Catalyzed Coupling Reaction between Electron‐Deficient Alkenyl Ethers with Silyl Enolates for Stereoselective Synthesis of 1,5‐Dioxo‐alk‐2‐enes

Ist Teil von

• European journal of organic chemistry, 2021-01, Vol.2021 (1), p.77-81

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2021

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A coupling reaction of electron‐deficient alkenyl ethers with silyl enolates catalyzed by InBr3 was achieved. Various silyl enolates and 2‐carbonylalkenyl ethers were applicable, giving the corresponding 1,5‐dioxo‐alk‐2‐enes with perfect stereoselectivity of the alkene moieties. The present coupling reaction proceeds via the 1,4‐addition of silyl enolates to alkenyl ethers followed by elimination of silyl alkoxides, in which moderate‐Lewis acidic InBr3 performs both the activation of alkenyl ethers and the elimination of alkoxy groups regardless of the presence of various coordinative functional groups. InBr3 catalysis enables the coupling between 2‐carbonylalkenyl ethers and silyl enolates to give 1,5‐dioxo‐alk‐2‐enes featuring alkene moieties with perfect stereoselectivity. Various types of 2‐carbonylalkenyl ethers and silyl enolates are applicable to the present reaction. InBr3 with moderate Lewis acidity plays an important role in both the activation of alkenyl ethers and in the elimination of alkoxy groups regardless of the presence of various coordinative functional groups.