Palladium(II)‐Catalyzed Enantioselective Azidation of Unactivated Alkenes

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 e...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-09, Vol.59 (39), p.17239-17244
Main Authors: Li, Xiaonan, Qi, Xiaoxu, Hou, Chuanqi, Chen, Pinhong, Liu, Guosheng
Format: Article
Language:English
Subjects:
Alkenes
asymmetric catalysis
azidopiperidines
Enantiomers
oxidative amination
Palladium
Reagents
unactivated alkenes
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Summary: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. A Pd‐catalyzed enantioselective intramolecular aminoazidation of unactivated alkenes using readily accessible 1‐azido‐1,2‐benziodoxol‐3(1H)‐one (ABX) as an azidating agent was established. This reaction affords a wide variety of structurally diverse 3‐N3‐substituted piperidines in good yields with excellent enantioselectivity, proceeds under mild reaction conditions, and features good functional‐group compatibility.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202006757