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A new tandem reaction of bifunctional peroxides enables the expedient synthesis of functionalized dihydrofurans
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-12-03 , DOI: 10.1039/d4qo01940g
Jiayi He, Yiwei Chen, Yukun Zhao, Lin Hu

Bifunctional peroxides are versatile reagents. Herein, we report a new annulation mode of peroxy enals that undergo a distinctive cascade reaction with β-keto esters under DBU basic conditions at room temperature, with the cascade specifically involving deconjugative epoxidation and aldol addition/cyclization. The reaction could rapidly construct complex dihydrofurans bearing adjacent quaternary–tertiary carbon centers and multiple functional groups with high diastereoselectivities.

中文翻译:


双功能过氧化物的新型串联反应使功能化二氢呋喃的合成成为可能



双功能过氧化物是多功能试剂。在此,我们报道了一种新的过氧烯醛环化模式,它在室温下在 DBU 碱性条件下与 β-酮酯发生独特的级联反应,该级联反应特别涉及解位环氧化和羟醛添加/环化。该反应可以快速构建复杂的二氢呋喃,这些呋喃带有相邻的季-叔碳中心和具有高非对映选择性的多个官能团。
更新日期:2024-12-03
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