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钯(II)催化的未活化烯烃的对映选择性叠氮化反应

Palladium(II)-Catalyzed Enantioselective Azidation of Unactivated Alkenes.

作者信息

Li Xiaonan, Qi Xiaoxu, Hou Chuanqi, Chen Pinhong, Liu Guosheng

机构信息

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

Chang-Kung Chuang Institute, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, China.

出版信息

Angew Chem Int Ed Engl. 2020 Sep 21;59(39):17239-17244. doi: 10.1002/anie.202006757. Epub 2020 Jul 29.

Abstract

The first Pd-catalyzed enantioselective azidation of unactivated alkenes has been established by using readily accessible 1-azido-1,2-benziodoxol-3(1H)-one (ABX) as an azidating reagent, which affords a wide variety of structurally diverse 3-N -substituted piperidines in good yields with excellent enantioselectivity. The reaction features good functional-group compatibility and mild reaction conditions. Notably, both an electrophilic azidating reagent and the sterically bulky chiral pyridinyl-oxazoline (Pyox) ligand are crucial to the successful reaction.

摘要

通过使用易于获得的1-叠氮基-1,2-苯并碘氧杂环戊-3(1H)-酮(ABX)作为叠氮试剂,首次实现了钯催化的未活化烯烃对映选择性叠氮化反应,该反应能以良好的产率和优异的对映选择性提供多种结构多样的3-N-取代哌啶。该反应具有良好的官能团兼容性和温和的反应条件。值得注意的是,亲电叠氮试剂和空间位阻较大的手性吡啶基恶唑啉(Pyox)配体对反应的成功都至关重要。

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