6533b852fe1ef96bd12aa478
RESEARCH PRODUCT
Tandem Nucleophilic Addition−Intramolecular Aza-Michael Reaction: Facile Synthesis of Chiral Fluorinated Isoindolines
Javier Ruiz MoscardóPablo BarrioElsa RodríguezSantos FusteroMaría Sánchez-rosellósubject
Models MolecularAza CompoundsIndolesTrifluoromethylNucleophilic additionHalogenationMolecular StructureTandemHydrolysisOrganic ChemistryStereoisomerismIsoindolesBiochemistryMedicinal chemistrychemistry.chemical_compoundCascade reactionchemistryNucleophileIntramolecular forceMichael reactionOrganic chemistryStereoselectivityPhysical and Theoretical Chemistrydescription
A highly stereoselective synthesis of fluorinated 1,3-disubstituted isoindolines is described. To this end, a tandem reaction consisting of a diastereoselective addition of fluorinated nucleophiles to Ellman's N-(tert-butanesulfinyl)imines followed by an intramolecular aza-Michael reaction has been developed. This strategy allows for the construction of isoindolines bearing several degrees of fluorination (mono-, di-, or trifluoromethyl as well as heavier fluorinated groups). In the majority of all cases, the products are formed as single isomers.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-01-01 | Organic Letters |