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以CsOCF为三氟甲氧基源的钯(II)催化未活化烯烃的对映选择性氨三氟甲氧基化反应

Palladium(II)-Catalyzed Enantioselective Aminotrifluoromethoxylation of Unactivated Alkenes using CsOCF as a Trifluoromethoxide Source.

作者信息

Chen Chaohuang, Pflüger Philipp Miro, Chen Pinhong, Liu Guosheng

机构信息

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, Münster, 48149, Germany.

出版信息

Angew Chem Int Ed Engl. 2019 Feb 18;58(8):2392-2396. doi: 10.1002/anie.201813591. Epub 2019 Jan 29.

Abstract

Asymmetric Pd -catalyzed intramolecular aminotrifluoromethoxylation of unactivated alkenes using readily accessible and stable CsOCF as a trifluoromethoxide source has been developed, which affords a wide variety of enantiomerically enriched β-substituted OCF -containing piperidines in good yields. Introducing a sterically bulky group into pyridine-oxazoline (Pyox) ligands is crucial to increasing both reactivity and enantioselectivity for the reaction. Additionally, the reaction features good functional group compatibility and mild reaction conditions.

摘要

利用易于获得且稳定的CsOCF作为三氟甲氧基源,开发了不对称钯催化的未活化烯烃分子内氨三氟甲氧基化反应,该反应能以良好的产率提供多种对映体富集的含β-取代OCF的哌啶。将空间位阻较大的基团引入吡啶-恶唑啉(Pyox)配体对于提高反应的反应性和对映选择性至关重要。此外,该反应具有良好的官能团兼容性和温和的反应条件。

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