6533b82efe1ef96bd1293c48
RESEARCH PRODUCT
Catalytic Enantioselective Conjugate Alkynylation of β-Aryl-β-trifluoromethyl Enones Constructing Propargylic All-Carbon Quaternary Stereogenic Centers
Carlos VilaGonzalo BlayAmparo Sanz-marcoJosé R. Pedrosubject
Trifluoromethyl010405 organic chemistryArylOrganic ChemistryChiral ligandEnantioselective synthesisDiethylzinc010402 general chemistry01 natural sciencesBiochemistryCombinatorial chemistry0104 chemical sciencesStereocenterCatalysischemistry.chemical_compoundchemistryPhysical and Theoretical ChemistryConjugatedescription
The enantioselective conjugate alkynylation of β-aryl-β-trifluoromethyl enones has been carried out using terminal alkynes and diethylzinc in the presence of 3,3'-bis(perfluorophenyl)BINOL as the chiral ligand to give the corresponding ketones bearing a trifluoromethylated propargylic quaternary stereocenter with fair to good enantioselectivities. Enones bearing a bulky 2-naphthyl attached to the carbonyl group provided the best enantioselectivities. The synthetic applicability of the resulting products has been demonstrated with their iodocyclization to form 4H-pyrans.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-07-16 | Organic Letters |