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Asymmetric Synthesis Of α-Fluoro-β-Amino-oxindoles With Tetrasubstituted C-F Stereogenic Centers Via Cooperative Cation-Binding Catalysis.

Sushovan Paladhi, S. Park, J. Yang, C. E. Song
Published 2017 · Chemistry, Medicine

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Biologically relevant chiral 3,3-disubstituted oxindole products containing a β-fluoroamine unit are obtained in high yields and with excellent stereoselectivity (up to 99% ee, dr >20:1 for syn) through the organocatalytic direct Mannich reaction of 3-fluoro-oxindoles as fluoroenolate precursors and α-amidosulfones as the bench-stable precursors of sensitive imines by using a chiral oligoethylene glycol and KF as a cation-binding catalyst and base, respectively. This protocol can be easily scaled without compromising the asymmetric induction. Furthermore, this protocol was also successfully extended to generate tetrasubstituted C-Cl and C-Br stereogenic centers.
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