Palladium-Catalyzed Aminomethylation and Cyclization of Enynol to O-Heterocycle Confined 1,3-Dienes

The rational tuning of the electrophilicity of the allylpalladium intermediates enables the regioselectively intramolecular 1,2-addition of enynol in the presence of aminal. This aminomethylation and cyclization reaction via C-N bond activation and intramolecular nucleophilic addition provides a rar...

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Bibliographic Details
Published in:Organic letters 2021-05, Vol.23 (10), p.3891-3896
Main Authors: Yu, Houjian, Yu, Bangkui, Zhang, Haocheng, Huang, Hanmin
Format: Article
Language:English
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Summary:The rational tuning of the electrophilicity of the allylpalladium intermediates enables the regioselectively intramolecular 1,2-addition of enynol in the presence of aminal. This aminomethylation and cyclization reaction via C-N bond activation and intramolecular nucleophilic addition provides a rare example for the synthesis of O-containing heterocycle-confined 1,3-dienes, which is of synthetic potential for further derivatization. The method possesses broad substrate generality as well as functional group compatibility and efficiently affords a wide range of desired products with 5-, 6-, and 8-membered O-containing heterocycles with various functional groups.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01019