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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (10), p. 1383-1389, 2014

DOI: 10.3762/bjoc.10.141

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Asymmetric Ugi 3CR on isatin-derived ketimine: Synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives

Journal article published in 2014 by Giordano Lesma, Fiorella Meneghetti, Alessandro Sacchetti, Mattia Stucchi, Alessandra Silvani ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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.