6533b7d4fe1ef96bd1262050
RESEARCH PRODUCT
Highly enantioselective copper(I)-catalyzed conjugate addition of terminal alkynes to 1,1-difluoro-1-(phenylsulfonyl)-3-en-2-ones: new ester/amide surrogates in asymmetric catalysis.
Gonzalo BlayAmparo Sanz-marcoJosé R. PedroIsabel FernándezAndrea Garcia‐ortizsubject
TrifluoromethylOrganic ChemistryEnantioselective synthesischemistry.chemical_elementGeneral ChemistryCopperCatalysisCatalysischemistry.chemical_compoundchemistryAlkynylationAmideOrganic chemistryConjugatedescription
A highly enantioselective copper-catalyzed conjugate alkynylation of monoactivated enones, namely 1,1-difluoro-1-(phenylsulfonyl)-3-en-2-ones, is described. The reaction products are obtained with good yields and excellent enantioselectivities (from 92 to 99% ee). The β-alkynylated difluoro(phenylsulfonyl) ketones can be converted into the corresponding β-alkynylated difluoro- and trifluoromethyl ketones, esters and amides. This is the first example on the use of 1,1-difluoro-1-(phenylsulfonyl)-3-en-2-ones as substrates in an enantioselective reaction, which have been shown to be new ester/amide surrogates.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-12-12 | Chemistry (Weinheim an der Bergstrasse, Germany) |