A Three Component Protocol for the Synthesis of Aziridines using BF3·(OEt)2

Shaik Firoj Basha and Shaik Anwar*,

Division of Chemistry, Department of Sciences and Humanities, Vignan′s Foundation for Science, Technology and Research-VFSTR (Deemed to be University), Vadlamudi, Guntur-522213, India

*Corresponding author: Fax:+ 91 863 2534468; Tel: +91 863 2344700; E-mail: shaikanwarcu@gmail.com; drsa_sh@vignan.ac.in

Abstract

Synthesis of N-(1R,2S)-2-(bromo-3-oxo-1,3-diphenylpropyl)-4-methylbenzene sulfonamide and N-(1R,2S)-(2-bromo-3-oxo-1,3-diphenylpropyl)-4-methylbenzene sulfonamide was carried out by a three component reaction using phenacyl bromide, p-toluenesulfonamide and carboxyaldehyde in presence of mild Lewis acid such as BF3·(OEt)2 in dichloromethane. The synthetic utility of this protocol was carried out with syn-isomer to yield corresponding cis-aziridines. This protocol was operationally simple for a wide variety of substituted carboxaldehydes and substituted phenacyl bromides.

Keywords

Phenacyl bromide, Carboxaldehyde, Lewis acid, Aziridine.

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