6533b7d9fe1ef96bd126cef6
RESEARCH PRODUCT
Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis.
Carlos VilaGonzalo BlayPablo Martínez-pardoAmparo Sanz-marcoM. Carmen MuñozJosé R. Pedrosubject
Trifluoromethyl010405 organic chemistryArylOrganic ChemistryEnantioselective synthesis010402 general chemistry01 natural sciencesCombinatorial chemistryCycloaddition0104 chemical sciencesStereocenterchemistry.chemical_compoundchemistryCatàlisiOrganocatalysisFISICA APLICADALewis acids and basesBifunctionalQuímica orgànicadescription
[EN] The first enantioselective formal [3 + 2] cycloaddition between ¿-isocyanoesters and trifluoromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a quaternary stereocenter substituted with a CF3 group, has been developed. The reaction is based upon a multicatalytic approach that combines a bifunctional Brønsted base-squaramide organocatalyst and Ag+ as Lewis acid. The reaction could be achieved with a range of aryl and heteroaryl trifluoromethyl ketones, and the resulting oxazolines were obtained with good to excellent diastereo- and enantioselectivity.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-01-01 | The Journal of organic chemistry |