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- Title
Asymmetric Desymmetrization via Metal-Free C−F Bond Activation: Synthesis of 3,5-Diaryl-5-fluoromethyloxazolidin-2-ones with Quaternary Carbon Centers.
- Authors
Tanaka, Junki; Suzuki, Satoru; Tokunaga, Etsuko; Haufe, Günter; Shibata, Norio
- Abstract
We disclose the first asymmetric activation of a non-activated aliphatic C−F bond in which a conceptually new desymmetrization of 1,3-difluorides by silicon-induced selective C−F bond scission is a key step. The combination of a cinchona alkaloid based chiral ammonium bifluoride catalyst and N,O-bis(trimethylsilyl)acetoamide (BSA) as the silicon reagent enabled the efficient catalytic cycle of asymmetric Csp3−F bond cleavage under mild conditions with high enantioselectivities. The ortho effect of the aryl group at the prostereogenic center is remarkable. This concept was applied for the asymmetric synthesis of promising agrochemical compounds, 3,5-diaryl-5-fluoromethyloxazolidin-2-ones bearing a quaternary carbon center.
- Subjects
FLUORINE analysis; CARBON-carbon bonds; LEWIS acids; BENZYLIC group; FLUORINE compounds
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 32, p9432
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201603210