Construction of Enantioenriched 9H‑Fluorene Frameworks via a Cascade Reaction Involving Remote Vinylogous Dynamic Kinetic Resolution

The benzylic C–H group of α,α-dicyanoolefins from 3-substituted 1-indanones could be significantly activated via transmission along the aromatic system, thus enabling dynamic kinetic resolution via a traditional reversible deprotonation–protonation process. Enantioenriched 9-substituted 9H-fluorene...

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Bibliographic Details
Published in:Organic letters 2020-11, Vol.22 (22), p.8973-8977
Main Authors: Hu, Cui-Xia, Chen, Lin, Hu, Di, Song, Xue, Chen, Zhi-Chao, Du, Wei, Chen, Ying-Chun
Format: Article
Language:English
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Summary:The benzylic C–H group of α,α-dicyanoolefins from 3-substituted 1-indanones could be significantly activated via transmission along the aromatic system, thus enabling dynamic kinetic resolution via a traditional reversible deprotonation–protonation process. Enantioenriched 9-substituted 9H-fluorene frameworks were finally constructed through an asymmetric vinylogous Michael addition to nitroolefins, followed by a cascade cyclization and oxidative aromatization process, under the catalysis of a chiral bifunctional thiourea-tertiary amine.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03372