Direct Asymmetric Dearomatization of Pyridines and Pyrazines by Iridium-Catalyzed Allylic Amination Reactions

The first iridium‐catalyzed intramolecular asymmetric allylic dearomatization reaction of pyridines and pyrazines has been realized. 2,3‐Dihydroindolizine and 6,7‐dihydropyrrolo[1,2‐a]pyrazine derivatives were obtained with excellent yields and enantioselectivity. This methodology features dearomati...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-07, Vol.53 (27), p.6986-6989
Main Authors: Yang, Ze-Peng, Wu, Qing-Feng, You, Shu-Li
Format: Article
Language:English
Subjects:
Alkylation
allylic compounds
Aromaticity
asymmetric catalysis
Asymmetry
cyclization
Derivatives
heterocycles
iridium
Methodology
Pyrazines
Pyridines
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Summary:The first iridium‐catalyzed intramolecular asymmetric allylic dearomatization reaction of pyridines and pyrazines has been realized. 2,3‐Dihydroindolizine and 6,7‐dihydropyrrolo[1,2‐a]pyrazine derivatives were obtained with excellent yields and enantioselectivity. This methodology features dearomatization by direct N‐allylic alkylation of pyridines or pyrazines under mild reaction conditions. Getting ‘rid’ of aromaticity: An iridium‐catalyzed intramolecular asymmetric allylic dearomatization reaction converts pyridines and pyrazines (not shown) into 2,3‐dihydroindolizine and 6,7‐dihydropyrrolo[1,2‐a]pyrazine derivatives with excellent yields and enantioselectivities. The dearomatization proceeds by direct N‐allylic alkylation of pyridines or pyrazines under mild reaction conditions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201404286