6533b820fe1ef96bd127a60a
RESEARCH PRODUCT
Chiral Monofluorobenzyl Carbanions: Synthesis of Enantiopure β‐Fluorinated β‐Phenylethylamines
Ascensión Sanz‐tejedorYolanda ArroyoSantos FusteroJosé L. García RuanoCarlos Del PozoInés AlonsoAlejandro Parrasubject
AnionsHalogenationStereochemistryOrganic ChemistryMolecular ConformationEnantioselective synthesisStereoisomerismGeneral ChemistryCatalysischemistry.chemical_compoundEnantiopure drugchemistryBenzyl CompoundsPhenethylaminesIonic liquidStereoselectivityEpimerIminesCarbaniondescription
The preparation of a stabilized monofluorobenzyl carbanion by means of a remote homochiral sulfinyl group and its completely stereoselective reactions with N-p-tolylsulfinylimines are described. The use of these reactions followed by the simultaneous removal of both chiral auxiliaries with tBuLi, which occurs without epimerization at the benzylic position, provides the quickest entry to enantiomerically pure β-fluorinated β-phenylethylamines.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-04-13 | Chemistry – A European Journal |