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

DOI :

10.3791/57572-v

August 22nd, 2018

August 22nd, 2018

8,183 Views

1Department of Chemistry, North Eastern Regional Institute of Science and Technology, 2Department of Chemistry, Hankuk University of Foreign Studies

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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Bicyclic Aziridinium Ions

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