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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
 

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Article DOI: 10.3791/57572-v • 11:45 min • August 22nd, 2018
August 22nd, 2018 •
1, 2
1Department of Chemistry, North Eastern Regional Institute of Science and Technology, 2Department of Chemistry, Hankuk University of Foreign Studies

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Bicyclic aziridinium ions such as 1-azoniabicyclo[4.1.0]heptane tosylate were generated from 2-[4-tolenesulfonyloxybutyl]aziridine, which was utilized for the preparation of substituted piperidines and azepanes via regio- and stereospecific ring-expansion with various nucleophiles. This highly efficient protocol allowed us to prepare diverse azaheterocycles including natural products such as fagomine, febrifugine analogue and balanol.

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Keywords: Bicyclic Aziridinium Ions Azaheterocycles Bipyridine Azepine Tosylate Nucleophile Ring-opening Azoniabicyclo Dichloromethane Acetonitrile
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