Issue 15, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Alessandro Sacchetti,*a   Alessandra Silvani,*b   Francesco G. Gatti,a   Giordano Lesma,b   Tullio Pilatic  and  Beatrice Trucchib  

* Corresponding authors

a Politecnico di Milano, Dipartimento di Chimica, Materiali ed Ingegneria Chimica ‘Giulio Natta’, via Mancinelli 7, Milano, Italy
E-mail: alessandro.sacchetti@polimi.it
Tel: +39 223993017

b Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, via G. Venezian 21, Milano, Italy

c Istituto di Scienze e Tecnologie Molecolari – CNR, Via Golgi 19, Milano, Italy

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

DOI
https://doi.org/10.1039/C1OB05532A
Article type
Paper
Submitted
05 Apr 2011
Accepted
05 May 2011
First published
05 May 2011

Org. Biomol. Chem., 2011,9, 5515-5522

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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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