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

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journal contribution
posted on 11.11.2020, 21:03 by Cui-Xia Hu, Lin Chen, Di Hu, Xue Song, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
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.