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. 2011 Aug 7;9(15):5515-22.
doi: 10.1039/c1ob05532a. Epub 2011 Jun 17.

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

Alessandro Sacchetti  1 , Alessandra Silvani, Francesco G Gatti, Giordano Lesma, Tullio Pilati, Beatrice Trucchi
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Free article

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

Alessandro Sacchetti et al. Org Biomol Chem. .
Free article

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.

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