title: Addition of TMSCN to chiral ketimines derived from isatin. Synthesis of an oxindole-based peptidomimetic and a bioactive spirohydantoin.
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.
authors.affiliation: Politecnico di Milano, Dipartimento di Chimica, Materiali ed Ingegneria Chimica Giulio Natta, via Mancinelli 7, 20131, Milano, Italy. alessandro.sacchetti@polimi.it
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sacchetti
authors.forename: Alessandra
authors.initials: A
authors.lastname: Silvani
authors.forename: Francesco G
authors.initials: FG
authors.lastname: Gatti
authors.forename: Giordano
authors.initials: G
authors.lastname: Lesma
authors.forename: Tullio
authors.initials: T
authors.lastname: Pilati
authors.forename: Beatrice
authors.initials: B
authors.lastname: Trucchi
mesh_terms: D018360:Crystallography, X-Ray; D003486:Cyanides / Q000737:chemistry*; D006827:Hydantoins / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D000078183:Oxindoles; D057786:Peptidomimetics; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D003486:Cyanides; D006827:Hydantoins; D007097:Imines; D007211:Indoles; D009570:Nitriles; D000078183:Oxindoles; D057786:Peptidomimetics; D013141:Spiro Compounds; D014297:Trimethylsilyl Compounds; C542835:ketimine; C022960:2-oxindole; C058010:trimethylsilyl cyanide; D007510:Isatin