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

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InBr3‐Catalyzed Coupling Reaction between Electron‐Deficient Alkenyl Ethers with Silyl Enolates for Stereoselective Synthesis of 1,5‐Dioxo‐alk‐2‐enes
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2020-10-27 , DOI: 10.1002/ejoc.202001342
Shuichi Nakao ₁ , Miki Saikai ₁ , Yoshihiro Nishimoto ₁ , Makoto Yasuda ₁

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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.

中文翻译：

InBr3催化的电子不足的烯基醚与甲硅烷基烯醇酸酯的立体选择性合成1,5-二氧代烷-2-烯

InBr ₃催化使2羰基链烯基醚和甲硅烷基烯醇酸酯之间偶联，可得到具有理想立体选择性的具有烯烃部分的1,5-二氧代烷-2-烯。各种类型的2-羰基烯基醚和甲硅烷基烯醇盐都可用于本反应。路易斯酸度适中的InBr ₃在烯基醚的活化和烷氧基的消除中都起着重要的作用，而与各种配位官能团的存在无关。

更新日期：2021-01-05

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