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

作者：Sacchetti Alessandro^*; Silvani Alessandra; Gatti Francesco G; Lesma Giordano; Pilati Tullio; Trucchi Beatrice

来源：Organic and Biomolecular Chemistry, 2011, 9(15): 5515-5522.

DOI：10.1039/c1ob05532a

We investigated the Strecker-type reaction of isatin derived chiral ketimines with TMSCN in the presence of a Lewis acid. The desired alpha-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.

• 出版日期2011