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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A practical method for the aziridination of α,β-unsaturated carbonyl compounds with a simple carbamate utilizing
Takehiro Umeda1, Satoshi Minakata1
1Department of Applied Chemistry, Graduate of Engineering, Osaka University Yamadaoka 2-1 Suita Osaka 565-0871 Japan minakata@chem.eng.osaka-u.ac.jp.
Abstract:
The efficient formation of tert-butyl N-chloro-N-sodio-carbamate by the reaction of simple tert-butyl carbamate with sodium hypochlorite pentahydrate (NaOCl·5H2O) would be a practical and green method for the aziridination of α,β-unsaturated carbonyl compounds. The process described herein is transition-metal free, all of the materials are commercially available, the byproducts (NaCl and H2O) are environmentally benign and the reaction is stereoselective. The resulting aziridines are potential precursors of amino acids.
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