π-Lewis-Base-Catalyzed Asymmetric Vinylogous Umpolung Reactions of Cyclopentadienones and Tropone,Angewandte Chemie International Edition

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π-Lewis-Base-Catalyzed Asymmetric Vinylogous Umpolung Reactions of Cyclopentadienones and Tropone
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-10-07 , DOI: 10.1002/anie.202111708
Xing-Xing Yang ₁ , Ru-Jie Yan ₁ , Guang-Yao Ran ₁ , Chen Chen ₁ , Jing-Fei Yue ₁ , Xiao Yan ₂ , Qin Ouyang ₂ , Wei Du ₁ , Ying-Chun Chen _{1,

2}

Affiliation

π-Allylpalladium-based 1,2-carbodipoles were generated from the carbonate derivatives of 4-hydroxy-2-cyclopentenones and isomerized in situ to electronically neutral η²-Pd⁰-cyclopentadienone complexes. These HOMO-raised cyclopentadienones participate, via π-Lewis base activation, in inverse-electron-demand Diels–Alder-type cycloadditions and cascade Morita–Baylis–Hillman- or Rauhut–Currier-type addition/allylic substitution reactions with diverse electrophiles.

中文翻译：

π-刘易斯碱催化的环戊二烯酮和托酮的不对称乙烯基Umpolung反应

π-烯丙基钯基 1,2-碳二极化合物由 4-羟基-2-环戊烯酮的碳酸酯衍生物产生，并原位异构化为电子中性 η ² -Pd ⁰ -环戊二烯酮配合物。这些 HOMO 引发的环戊二烯酮通过 π-刘易斯碱活化参与反电子需求 Diels-Alder 型环加成和级联 Morita-Baylis-Hillman 或 Rauhut-Currier 型加成/烯丙基取代反应与不同的亲电子试剂。

更新日期：2021-12-06

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