Highly Enantioselective Ruthenium/PNNP-Catalyzed Imine Aziridination: Evidence of Carbene Transfer from a Diazoester Complex

…, M Ranocchiari, A Schira, C Schotes, A Mezzetti

Index: Egloff, Joel; Ranocchiari, Marco; Schira, Amata; Schotes, Christoph; Mezzetti, Antonio Organometallics, 2013 , vol. 32, # 16 p. 4690 - 4701

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Citation Number: 20

Abstract

The ruthenium/PNNP complexes [RuCl (Et2O)(PNNP)] Y (Y= PF6, 4 PF6; BF4, 4 BF4; or SbF6, 4 SbF6)(10 mol%) catalyze the enantioselective aziridination of imines with ethyl diazoacetate (EDA) as carbene source (PNNP=(1 S, 2 S)-N, N′-bis [o-(diphenylphosphino) benzylidene] cyclohexane-1, 2-diamine). The highest enantioselectivity was obtained with 4 SbF6, which aziridinated N-benzylidene-1, 1-diphenylmethanamine (5a) to cis-ethyl 1- ...