title: Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives.
abstract: An efficient Ugi three-component reaction of a preformed chiral ketimine derived from isatin with various isonitrile and acid components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction of the amine chiral residue. A wide variety of novel chiral 3,3-disubstituted 3-aminooxindoles were obtained, a selection of which were subjected to post-Ugi transformations, paving the way to application as peptidomimetics.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, via C. Golgi, 19, 20133 Milano (Italy).
authors.forename: Giordano
authors.initials: G
authors.lastname: Lesma
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via L. Mangiagalli 25, 20133 Milano, Italy.
authors.forename: Fiorella
authors.initials: F
authors.lastname: Meneghetti
authors.affiliation: Dipartimento di Chimica, Materiali e Ingegneria Chimica 'Giulio Natta', Politecnico di Milano, p.zza Leonardo da Vinci 32, 20133 Milano, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sacchetti
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, via C. Golgi, 19, 20133 Milano (Italy).
authors.forename: Mattia
authors.initials: M
authors.lastname: Stucchi
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, via C. Golgi, 19, 20133 Milano (Italy).
authors.forename: Alessandra
authors.initials: A
authors.lastname: Silvani
keywords: Ugi; isatin; multicomponent; oxindole; peptidomimetics