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Chemistry

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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

Kapitel

Summary

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.

Tags

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