4.7 Article

Diastereoselective and Enantioselective Epoxidation of Acyclic β-Trifluoromethyl-β,β-Disubstituted Enones by Hydrogen Peroxide with a Pentafluorinated Quinidine-Derived Phase-Transfer Catalyst

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 10, Pages 1917-1923

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300249

Keywords

asymmetric catalysis; epoxidation; hydrogen peroxide; phase-transfer catalysts; trifluoromethyl group

Funding

  1. NSFC [21172018]
  2. Beijing Institute of Technology

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An efficient catalytic asymmetric epoxidation of -trifluoromethyl-,-disubstituted unsaturated ketones has been achieved by a pentafluorine-substituted phase-transfer catalyst with hydrogen peroxide (30%). 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.

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