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.
Addition of TMSCN to chiral ketimines derived from isatin : Synthesis of an oxindole-based peptidomimetic and a bioactive spirohydantoin / A. Sacchetti, A. Silvani, F. Gatti, G. Lesma, T. Pilati, B. Trucchi. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 9:15(2011), pp. 5515-5522.
Addition of TMSCN to chiral ketimines derived from isatin : Synthesis of an oxindole-based peptidomimetic and a bioactive spirohydantoin
A. SilvaniSecondo
;G. Lesma;B. TrucchiUltimo
2011
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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