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Synthesis 2010(20): 3423-3428
DOI: 10.1055/s-0030-1257913
DOI: 10.1055/s-0030-1257913
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkAn Improved and Mild Wenker Synthesis of Aziridines
Further Information
Received
25 May 2010
Publication Date:
30 July 2010 (online)
Publication History
Publication Date:
30 July 2010 (online)
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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