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.
Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives / G. Lesma, F. Meneghetti, A. Sacchetti, M. Stucchi, A. Silvani. - In: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1860-5397. - 10(2014), pp. 1383-1389.
Titolo: | Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives |
Autori: | |
Parole Chiave: | Isatin; Multicomponent; Oxindole; Peptidomimetics; Ugi |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 2014 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.3762/bjoc.10.141 |
Appare nelle tipologie: | 01 - Articolo su periodico |