(E)-Trifluoromethyl imines were considered as ideal substrates to be transformed into the corresponding diaziridines by a direct amination reaction with nosyloxycarbamates. The diastereoselective induction was strongly controlled by the N-substituent Similar results were obtained in the epoxidation reactions performed on the same substrates using m-CPBA as oxidant. Starting from enantiopure imines chiral diaziridines or oxaziridines were obtained with very high enantiopurity. (C) 2011 Elsevier Ltd. All rights reserved.
Synthesis of optically active trifluoromethyl substituted diaziridines and oxaziridines / Laura, Carroccia; Fioravanti, Stefania; Pellacani, Lucio; Sadun, Claudia; Tardella, Paolo Antonio. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 67:30(2011), pp. 5375-5381. [10.1016/j.tet.2011.05.097]
Synthesis of optically active trifluoromethyl substituted diaziridines and oxaziridines
FIORAVANTI, Stefania;PELLACANI, Lucio;SADUN, Claudia;TARDELLA, Paolo Antonio
2011
Abstract
(E)-Trifluoromethyl imines were considered as ideal substrates to be transformed into the corresponding diaziridines by a direct amination reaction with nosyloxycarbamates. The diastereoselective induction was strongly controlled by the N-substituent Similar results were obtained in the epoxidation reactions performed on the same substrates using m-CPBA as oxidant. Starting from enantiopure imines chiral diaziridines or oxaziridines were obtained with very high enantiopurity. (C) 2011 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
