title: Bifunctional phase-transfer catalysis in the asymmetric synthesis of biologically active isoindolinones.
abstract: New bifunctional chiral ammonium salts were investigated in an asymmetric cascade synthesis of a key building block for a variety of biologically relevant isoindolinones. With this chiral compound in hand, the development of further transformations allowed for the synthesis of diverse derivatives of high pharmaceutical value, such as the Belliotti (S)-PD172938 and arylated analogues with hypnotic sedative activity, obtained in good overall total yield (50%) and high enantiomeric purity (95% ee). The synthetic routes developed herein are particularly convenient in comparison with the current methods available in literature and are particularly promising for large scale applications.
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy; Dipartimento di Farmacia, Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy.
authors.forename: Antonia
authors.initials: A
authors.lastname: Di Mola
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz Altenbergerstraße 69, 4040 Linz, Austria.
authors.forename: Maximilian
authors.initials: M
authors.lastname: Tiffner
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Scorzelli
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy.
authors.forename: Laura
authors.initials: L
authors.lastname: Palombi
authors.affiliation: Dipartimento di Medicina Sperimentale, Università di Napoli, Napoli, Italy.
authors.forename: Rosanna
authors.initials: R
authors.lastname: Filosa
authors.affiliation: Dipartimento di Farmacia, Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: De Caprariis
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz Altenbergerstraße 69, 4040 Linz, Austria.
authors.forename: Mario
authors.initials: M
authors.lastname: Waser
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Massa
keywords: Belliotti (S)-PD 172938; asymmetric synthesis; heterocycles; isoindolinones cascade reactions; phase transfer catalysts