A novel N,N-dibenzyl diaminomethylenemalononitrile organocatalyst efficiently promoted asymmetric Henry reactions of trifluoromethyl enones with nitromethane, affording corresponding highly functionalized products in high yields with excellent enantioselectivities (up to 90% ee). This study is the first to report the successful example of the asymmetric 1,2-additions of nitromethane to trifluoromethyl enones.
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Article Synopsis
- A new strategy was created to transform β-trifluoromethyl enones through a three-step process: carbonyl reduction, hydrodefluorination, and defluoroamination, all without using transition metals.
- This approach successfully produced useful α-fluoroenamides in high yields, which can further be converted into important organofluorides and heterocycles.
- The carbonyl group aids in the reaction by affecting both the electronic and steric properties of the molecules, making the defluorination process more controllable and selective.
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