An Improved and Mild Wenker
Synthesis of Aziridines

Xinyao Li; Ning Chen; Jiaxi Xu

doi:10.1055/s-0030-1257913

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Synthesis 2010(20): 3423-3428
DOI: 10.1055/s-0030-1257913

PAPER

An Improved and Mild Wenker Synthesis of Aziridines

Xinyao Li, Ning Chen, Jiaxi Xu*
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China
Fax: +86(10)64435565; e-Mail: jxxu@mail.buct.edu.cn;

Further Information

Publication History

Received 25 May 2010
Publication Date:
30 July 2010 (online)

Abstract
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Abstract

The conventional Wenker synthesis of aziridines from vicinal amino alcohols has been modified by employing mild reaction conditions. Amino alcohols were converted into their hydrogen sulfates with chlorosulfonic acid. The sulfates were cyclized with sodium hydroxide, and even with non-nucleophilic sodium carbonate. The current, improved method extends the scope of the typical Wenker synthesis and is applicable to unstable amino alcohols in hot sulfuric acid and to unstable sulfates which favor elimination and hydroxide displacement in the presence of strong base.

Key words

amino alcohols - aziridines - hydrogen sulfates - Wenker synthesis

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