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

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...

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Published inBeilstein journal of organic chemistry Vol. 10; no. 1; pp. 1383 - 1389
Main Authors Lesma, Giordano, Meneghetti, Fiorella, Sacchetti, Alessandro, Stucchi, Mattia, Silvani, Alessandra
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 18.06.2014
Subjects
Chemistry
Full Research Paper
isatin
multicomponent
oxindole
peptidomimetics
Ugi
oxindole
peptidomimetics
isatin
Ugi
multicomponent
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Summary: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.
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.10.141