Premium
Diastereoselective and Enantioselective Epoxidation of Acyclic β‐Trifluoromethyl‐β,β‐Disubstituted Enones by Hydrogen Peroxide with a Pentafluorinated Quinidine‐Derived Phase‐Transfer Catalyst
Author(s) -
Wu Shaoxiang,
Pan Dong,
Cao Chengyao,
Wang Qi,
Chen FuXue
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300249
Subject(s) - chemistry , trifluoromethyl , enantioselective synthesis , catalysis , hydrogen peroxide , organic chemistry , phase transfer catalyst , combinatorial chemistry , alkyl
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.