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通过镍催化的碳-碳键活化实现苯并环丁酮与降冰片二烯的立体选择性[2+2+2]环加成反应。

Stereoselective [2 + 2 + 2] Cycloaddition of Benzocyclobutanones and Norbornadienes through Nickel-Catalyzed C-C Bond Activation.

作者信息

Richter Robert C, Lindenmaier Ivo H, Schray David, Ströbele Markus, Fleischer Ivana

机构信息

Institute of Organic Chemistry, Faculty of Science, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.

Institute of Inorganic Chemistry, Faculty of Science, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.

出版信息

Org Lett. 2025 May 30;27(21):5385-5389. doi: 10.1021/acs.orglett.5c01324. Epub 2025 May 16.

DOI:10.1021/acs.orglett.5c01324
PMID:40377945
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12131216/
Abstract

We report a nickel-catalyzed stereoselective [2 + 2 + 2] cycloaddition between norbornadienes and benzocyclobutanones via C-C activation. This transformation generates four stereocenters, producing nortricyclane scaffolds that introduce three-dimensional architecture. The reaction proceeds with high stereoselectivity while allowing precise steric control of the reaction site, offering a versatile approach for constructing intricate stereochemical frameworks.

摘要

我们报道了一种镍催化的降冰片二烯与苯并环丁酮之间通过碳-碳活化进行的立体选择性[2 + 2 + 2]环加成反应。这种转化生成了四个立体中心,产生了引入三维结构的降三环骨架。该反应以高立体选择性进行,同时允许对反应位点进行精确的空间控制,为构建复杂的立体化学骨架提供了一种通用方法。

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本文引用的文献

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Deconstructive Synthesis of Bridged and Fused Rings via Transition-Metal-Catalyzed "Cut-and-Sew" Reactions of Benzocyclobutenones and Cyclobutanones.通过过渡金属催化的苯并环丁烯酮和环丁酮的“切缝”反应构建桥环和稠环
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Rhodium-Catalyzed (4+1) Cycloaddition between Benzocyclobutenones and Styrene-Type Alkenes.铑催化的苯并环丁烯酮与苯乙烯型烯烃之间的(4+1)环加成反应
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Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.手性钌催化苯并环丁烯酮-酮醇环加成反应:结合 C-C 键活化和转移氢化偶联构建 II 型聚酮。
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