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

被引:32
|
作者
Wu, Shaoxiang [1 ]
Pan, Dong [1 ]
Cao, Chengyao [1 ]
Wang, Qi [1 ]
Chen, Fu-Xue [1 ]
机构
[1] Beijing Inst Technol, Dept Appl Chem, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
关键词
asymmetric catalysis; epoxidation; hydrogen peroxide; phase-transfer catalysts; trifluoromethyl group; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; QUATERNARY AMMONIUM-SALT; ALPHA-AMINO-ACIDS; ASYMMETRIC EPOXIDATION; DUAL FUNCTIONS; KETONES; ALKYLATION; OXIDATION; REDUCTION; GENERATION;
D O I
10.1002/adsc.201300249
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
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.
引用
收藏
页码:1917 / 1923
页数:7
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