ol6b01516_si_002.cif (508.74 kB)

Detrifluoroacetylative in Situ Generation of Free 3‑Fluoroindolin-2-one-Derived Tertiary Enolates: Design, Synthesis, and Assessment of Reactivity toward Asymmetric Mannich Reactions

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posted on 15.06.2016 by Chen Xie, Lijun Zhang, Wanxing Sha, Vadim A. Soloshonok, Jianlin Han, Yi Pan
The discovery of detrifluoroacetylative in situ generation of a new type of fluorinated amide enolates derived from 3-fluoroindolin-2-one and their asymmetric Mannich additions with sulfinylaldimines bearing fluoroalkyl groups is reported, which afforded α-fluoro-β-(fluoroalkyl)-β-aminoindolin-2-ones containing C–F quaternary stereogenic centers with excellent yields and high diastereoselectivities.