Palladium(II)-Catalyzed Enantioselective Azidation of Unactivated Alkenes

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

doi:10.1002/anie.202006757

Palladium(II)-Catalyzed Enantioselective Azidation of Unactivated Alkenes

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

Authors

Xiaonan Li¹, Xiaoxu Qi¹, Chuanqi Hou¹, Pinhong Chen¹, Guosheng Liu^{1

2}

Affiliations

¹ 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.
² Chang-Kung Chuang Institute, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, China.

PMID: 32519504
DOI: 10.1002/anie.202006757

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-N₃ -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.

Keywords: asymmetric catalysis; azidopiperidines; oxidative amination; palladium; unactivated alkenes.

Abstract

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