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

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8,215 Views

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11:45 min

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August 22, 2018

DOI:

10.3791/57572-v

DOI:
10.3791/57572-v

•

11:45 min
August 22, 2018

•

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

Summary

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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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Yadav, N. N., Ha, H. Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles. J. Vis. Exp. (138), e57572, doi:10.3791/57572 (2018).

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