SN2-type ring opening of substituted-𝑁-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt

Journal of Chemical Sciences

Amit Kumar¹  Deo Prakash Tiwari¹  Kalpataru Das1¹  Manas K Ghorai¹ 

[1] Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India$$

关键词: Haloamines;    aziridines;    enantioselective;    Lewis acid;    nucleophilic ring opening;    quaternary ammonium salts.;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

Quaternary ammonium salt mediated highly regioselective ring opening of aziridines with zinc(II) halides to racemic and non-racemic 𝛽-halo amines in excellent yield and selectivity is described. The reaction proceeds via an SN2-type pathway and the partial racemization of the starting substrate and the product was effectively controlled by using quaternary ammonium salts to afford the enantioenriched products (er up to 95:5).

【 授权许可】

Unknown