Metal‐Catalyzed Spiroannulation‐Fluoromethylfunctionaliztions of 1,5‐Enynes for the Synthesis of Stereodefined (Z)‐Spiroindenes,Chemistry - An Asian Journal

当前位置： X-MOL 学术 › Chem. Asian J. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Metal‐Catalyzed Spiroannulation‐Fluoromethylfunctionaliztions of 1,5‐Enynes for the Synthesis of Stereodefined (Z)‐Spiroindenes
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2020-10-05 , DOI: 10.1002/asia.202000954
Hang-Dong Zuo ₁ , Chen-Chang Cui ₂ , Cheng Guo ₃ , Wen-Juan Hao ₂ , Shu-Jiang Tu ₂ , Bo Jiang ₄

Affiliation

Two classes of new catalytic spiroannulation‐fluormethylfunctionaliztions of para‐quinone methide (p‐QM)‐containing 1,5‐enynes have been established under redox‐neutral conditions. Palladium‐catalyzed spiroannulation‐iododifluoromethylation with ethyl difluoroiodoacetate oriented completely stereoselective access to (Z)‐spiroindenes and the latter included copper‐catalyzed three‐component spiroannulation‐cyanotrifluoromethylation starting from Togni's reagent and trimethylsilanecarbonitrile (TMSCN). Both reaction pathways involve fluoroalkyl radical‐triggered 1,6‐addition/5‐exo‐dig annulation/metal radical cross‐coupling/reductive elimination sequence, providing practical and stereoselective protocols for rapidly constructing cyclohexadienone‐containing spiroindenes with generally good yields.

中文翻译：

1,5-烯炔的金属催化螺环化-氟甲基官能化反应合成立体定义的（Z）-螺茚

两类新型催化spiroannulation-fluormethylfunctionaliztions对-quinone甲基化物（p -QM）含1,5-烯炔已被氧化还原中性条件下建立的。钯催化的二氟碘乙酸乙酯的螺环化-碘代二氟甲基化定向完全立体选择性地进入（Z）-螺吲哚，后者包括从Togni试剂和三甲基硅烷碳腈（TMSCN）开始的铜催化的三成分螺环化-氰基三氟甲基化。两个反应途径涉及氟代烷基触发1,6-加成/ 5-外型-挖环空/金属自由基交叉偶联/还原消除顺序，为快速构建通常具有良好收率的含环己二酮的螺二茚提供实用和立体选择的方案。

更新日期：2020-12-01

点击分享查看原文

点击收藏

阅读更多本刊最新论文