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Issue 15, 2011
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Addition of TMSCN to chiral ketimines derived from isatin. Synthesis of an oxindole-based peptidomimetic and a bioactive spirohydantoin

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Abstract

We investigated the Strecker-type reaction of isatin derived chiral ketimines with TMSCN in the presence of a Lewis acid. The desired α-amino nitriles have been obtained in good yields with moderate diastereoselectivity. Further elaboration of the cyanide group allowed the preparation of a new oxindole-based peptidomimetic and a pharmaceutically relevant spirohydantoin.

Graphical abstract: Addition of TMSCN to chiral ketimines derived from isatin. Synthesis of an oxindole-based peptidomimetic and a bioactive spirohydantoin

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Article information


Submitted
05 Apr 2011
Accepted
05 May 2011
First published
05 May 2011

Org. Biomol. Chem., 2011,9, 5515-5522
Article type
Paper

Addition of TMSCN to chiral ketimines derived from isatin. Synthesis of an oxindole-based peptidomimetic and a bioactive spirohydantoin

A. Sacchetti, A. Silvani, F. G. Gatti, G. Lesma, T. Pilati and B. Trucchi, Org. Biomol. Chem., 2011, 9, 5515
DOI: 10.1039/C1OB05532A

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