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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Published inAngewandte Chemie Vol. 132; no. 39; pp. 17392 - 17397
Main Authors Li, Xiaonan, Qi, Xiaoxu, Hou, Chuanqi, Chen, Pinhong, Liu, Guosheng
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 21.09.2020
Subjects
Alkenes
asymmetric catalysis
azidopiperidines
Chemistry
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.
Bibliography:In memory of Professor Kilian Muñiz
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202006757