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

Nagendra Nath Yadav; Hyun-Joon Ha

doi:10.3791/57572

Dziennik

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Chemia

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

JoVE Journal
Chemia

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JoVE Journal Chemia

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

8,332 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

•

6 Views

Nagendra Nath Yadav¹, Hyun-Joon Ha²

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

Transkrypcja

Podsumowanie

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.