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S N 2-type ring opening of substituted-N-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt

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Abstract

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).

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.

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  1. Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India

    MANAS K GHORAI, DEO PRAKASH TIWARI, AMIT KUMAR & KALPATARU DAS

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  1. MANAS K GHORAI
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GHORAI, M.K., TIWARI, D.P., KUMAR, A. et al. S N 2-type ring opening of substituted-N-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt. J Chem Sci 123, 951–961 (2011). https://doi.org/10.1007/s12039-011-0178-0

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