Asymmetric inverse-electron-demand hetero-diels-alder reaction for the construction of bicyclic skeletons with multiple stereocenters by using a bifunctional organocatalytic strategy: An efficient approach to chiral macrolides

Jiang X.; Wang L.; Kai M.; Zhu L.; Yao X.; Wang R.

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Asymmetric inverse-electron-demand hetero-diels-alder reaction for the construction of bicyclic skeletons with multiple stereocenters by using a bifunctional organocatalytic strategy: An efficient approach to chiral macrolides

机译：通过使用双功能有机催化策略构建具有多个立体中心的双环骨架的不对称逆电子需求杂狄尔斯-阿尔德反应：一种有效的手性大环内酯类化合物

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We have performed the first bifunctional organocatalytic highly enantioselective inverse-electron-demand hetero-Diels-Alder reaction of cyclic ketones with enones to afford densely functionalized bicyclic skeletons that contain three stereocenters (up 82 % yield, 10:1 d.r., and 97 % ee). Unlike the previous IEDDAR catalytic strategy, this method features a double HOMO _(dienophile)/ LUMO_(diene)-activated pathway. Moreover, this process provides a promising method for the construction of enantioenriched macrolides. Bicyclic exercises: A highly enantioselective inverse-electron- demand hetero-Diels-Alder reaction of cyclic ketones with enones affords functionalized bicyclic skeletons with three stereocenters that can be used for the construction of macrolides.

机译：我们已经完成了环酮与烯酮的首次双官能有机催化高对映选择性逆电子要求的异Diels-Alder反应，以提供包含三个立体中心的高官能化双环骨架（产率提高82％，dr降低10：1，ee降低97％））。与以前的IEDDAR催化策略不同，此方法具有双重HOMO_（dienophile）/ LUMO_（diene）活化途径。而且，该方法为构建对映体富集的大环内酯类化合物提供了有希望的方法。双环练习：环状酮与烯酮的高度对映选择性逆电子需求异Diels-Alder反应提供了具有三个立体中心的功能化双环骨架，可用于构建大环内酯类化合物。

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《Chemistry: A European journal》 |2012年第36期|共9页
作者
Jiang X.; Wang L.; Kai M.; Zhu L.; Yao X.; Wang R.;
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正文语种 eng
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asymmetric synthesis; bifunctional catalysts; enones; hetero-Diels-Alder reactions; ketones;

机译：不对称合成;双功能催化剂;烯类;杂-Diels-Alder反应;酮;

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1. Asymmetric inverse-electron-demand hetero-diels-alder reaction for the construction of bicyclic skeletons with multiple stereocenters by using a bifunctional organocatalytic strategy: An efficient approach to chiral macrolides [J] . Jiang X., Wang L., Kai M., Chemistry: A European journal . 2012,第36期

机译：通过使用双功能有机催化策略构建具有多个立体中心的双环骨架的不对称逆电子需求杂狄尔斯-阿尔德反应：一种有效的手性大环内酯类化合物
2. Bifunctional Organocatalytic Strategy for Inverse-Electron-Demand Diels-Alder Reactions: Highly Efficient In Situ Substrate Generation and Activation to Construct Azaspirocyclic Skeletons [J] . Xianxing Jiang, Xiaomei Shi, Should Wang Angewandte Chemie . 2012,第9期

机译：电子反需求Diels-Alder反应的双功能有机催化策略：高效的原位底物生成和激活以构建氮杂环的骨架。
3. Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Six-membered Cyclic Ketones: An Enamine/Metal Lewis Acid Bifunctional Approach [J] . Zhenghu Xu, Lu Liu, Kraig Wheeler Angewandte Chemie . 2011,第15期

机译：六元环酮的不对称反电子需求杂Diels-Alder反应：一种烯胺/金属路易斯酸双功能方法
4. Synthesis of Asymmetric Catalysts with an Efficient Chiral Amplification Based on the Feedback of the Reaction Products [C] . Yuuya Nagata, Fumiko Miyata, Michinori Suginome 日本化学会春季年会講演予稿集 . 2018

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5. (I) Synthesis and Application of Chiral Biphenol-Based Phosphorus Ligands to Catalytic Asymmetric Synthesis; (II) Rhodium-Catalyzed Cycloaddition Reactions for Rapid Construction of Polycyclic Skeletons of Biological Interest [D] . Chien, Chih-Wei 2013

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6. Asymmetric Synthesis of Spirocyclopentane OxindolesContaining Four Consecutive Stereocenters and Quaternary α-NitroEsters via Organocatalytic Enantioselective Michael–MichaelCascade Reactions [O] . PrakashD. Chaudhari, Bor-Cherng Hong, *, 2019

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Asymmetric inverse-electron-demand hetero-diels-alder reaction for the construction of bicyclic skeletons with multiple stereocenters by using a bifunctional organocatalytic strategy: An efficient approach to chiral macrolides

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