Regiodivergent and Stereospecific Aziridine Opening by Copper‐Catalyzed Addition of Silicon Grignard Reagents

다국어 초록 (Multilingual Abstract)

A stereospecific ring opening of various 2‐aryl‐substituted aziridines with silicon Grignard reagents under copper catalysis is reported. The regiochemical outcome is governed by the steric demand of the silicon nucleophile. The LiCl introduced with the magnesium reagent R3SiMgX⋅2 LiCl is shown to enhance the SN2‐type displacement of the carbon‐nitrogen bond by coordination to the aziridine nitrogen atom.
Everything under control: The ring opening of aziridines with silicon Grignard reagents was achieved under copper catalysis. The regioselectivity was determined by the size of the silicon nucleophile. The substitution of carbon‐nitrogen bond proceeded with inversion of configuration, and even fully substituted carbon atoms engaged in this SN2‐type reaction.