6533b7d1fe1ef96bd125d8f9
RESEARCH PRODUCT
Diastereoselective synthesis of 2-phenyl-3-(trifluoromethyl)piperazines as building blocks for drug discovery.
Michiel Van GoolAndrés A. TrabancoOscar DelgadoSantos FusteroMaría Sánchez-rosellóNatalia Mateusubject
TrifluoromethylNucleophilic additionHydrocarbons FluorinatedMolecular StructureChemistryDrug discoveryOrganic ChemistryStereoisomerismSilanesCombinatorial chemistryCatalysisPiperazineschemistry.chemical_compoundReagentDrug DiscoveryOrganic chemistryIndicators and Reagentsdescription
The synthesis of enantiomerically pure cis- and trans-2-phenyl-3-(trifluoromethyl)piperazines is described. It involved, as the key step, a diastereoselective nucleophilic addition of the Ruppert-Prakash reagent (TMSCF3) to alpha-amino sulfinylimines bearing Ellman's auxiliary. This methodology allows an entry into hitherto unknown trifluoromethylated and stereochemically defined piperazines, key scaffold components in medicinal chemistry.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-01-01 | The Journal of organic chemistry |