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. 2014 Jun 18:10:1383-9.
doi: 10.3762/bjoc.10.141. eCollection 2014.

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

Giordano Lesma  1 , Fiorella Meneghetti  2 , Alessandro Sacchetti  3 , Mattia Stucchi  1 , Alessandra Silvani  1
Affiliations

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

Giordano Lesma et al. Beilstein J Org Chem. .

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.

Keywords: Ugi; isatin; multicomponent; oxindole; peptidomimetics.

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Figures

Figure 1
Figure 1
Biologically active agents containing a 3-substituted-3-aminooxindole core.
Figure 2
Figure 2
ORTEP [37] view of one of the two independent molecules of 4a present in the asymmetric unit, showing the arbitrary atom-labelling scheme. Atomic displacement parameters for non-H atoms are at a probability level of 50%.
Figure 3
Figure 3
Proposed explanation of the stereochemical outcome of the Ugi 3CR.
Scheme 1
Scheme 1
Post-Ugi transformation on compound 10a.
Scheme 2
Scheme 2
Post-Ugi cyclization on compound 15a.
See this image and copyright information in PMC

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