Abstract
An efficient catalytic asymmetric epoxidation of β-trifluoromethyl- β,β-disubstituted unsaturated ketones has been achieved by a pentafluorine-substituted phase-transfer catalyst with hydrogen peroxide (30%). Thus, the β-trifluoromethyl-α,β-epoxy ketones with a quaternary carbon centre were obtained in excellent diastereoselectivities (up to 100:1 dr) and excellent enantioselectivities (up to 99.7% ee). Low catalyst loading, recycle of catalyst, environmentally benign oxidant and easy transformation of the epoxides into medicinally important trifluoromethylated intermediate make our protocol much more practical.
Original language | English |
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Pages (from-to) | 1917-1923 |
Number of pages | 7 |
Journal | Advanced Synthesis and Catalysis |
Volume | 355 |
Issue number | 10 |
DOIs | |
Publication status | Published - 8 Jul 2013 |
Keywords
- asymmetric catalysis
- epoxidation
- hydrogen peroxide
- phase-transfer catalysts
- trifluoromethyl group
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Wu, S., Pan, D., Cao, C., Wang, Q., & Chen, F. X. (2013). Diastereoselective and enantioselective epoxidation of acyclic β-trifluoromethyl-β,β-disubstituted enones by hydrogen peroxide with a pentafluorinated quinidine-derived phase-transfer catalyst. Advanced Synthesis and Catalysis, 355(10), 1917-1923. https://doi.org/10.1002/adsc.201300249