6533b82ffe1ef96bd1294eb5

RESEARCH PRODUCT

ChemInform Abstract: Tandem Nucleophilic Addition-Intramolecular Aza-Michael Reaction: Facile Synthesis of Chiral Fluorinated Isoindolines.

Javier Ruiz MoscardóPablo BarrioMaría Sánchez-rosellóSantos FusteroElsa Rodríguez

subject

chemistry.chemical_compoundNucleophilic additionTrifluoromethylTandemCascade reactionNucleophileChemistryIntramolecular forceMichael reactionStereoselectivityGeneral MedicineMedicinal chemistry

description

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.

yearjournalcountryeditionlanguage
2011-02-24ChemInform
https://doi.org/10.1002/chin.201112110