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RESEARCH PRODUCT
Synthesis of a New Fluorinated Oxazolidinone and Its Reactivity as a Chiral Auxiliary in Aldol Reactions.
Julio PieraSantos FusteroNatalia MateuJuan F. Sanz-cerveraPaula Bellosubject
Chiral auxiliaryImidoyl chlorideorganic chemicalsOrganic ChemistryEnantioselective synthesisDiastereomerSulfoxideGeneral MedicineBiochemistryCombinatorial chemistryInorganic Chemistrychemistry.chemical_compoundchemistryAldol reactionEnvironmental ChemistryOrganic chemistryBase Ratioheterocyclic compoundsReactivity (chemistry)Lewis acids and basesPhysical and Theoretical Chemistrydescription
A new enantiomerically pure fluorinated oxazolidinone has been prepared from a fluorinated imidoyl chloride and an optically pure sulfoxide. The diastereoselective reduction of the β-iminosulfoxide thus formed followed by elimination of the sulfoxide and cyclization of the created aminoalcohol furnishes the desired product. The fluorinated oxazolidinone was subsequently used as a chiral auxiliary in Aldol reactions. We also found that the selective formation of the syn-Evans and syn-non-Evans diastereoisomer can be controlled by adjusting the Lewis acid/base ratio.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2007-06-01 | ChemInform |