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Preparation of a Stable Bicyclic Aziridinium Ion and Its Ring Expansion toward Piperidines and Azepanes

Preparation of a Stable Bicyclic Aziridinium Ion and Its Ring Expansion toward Piperidines and... The formation of the stable form of 1‐azabicyclo[4.1.0]heptane tosylate was successfully achieved from 2‐[4‐tolenesulfonyloxybutyl]aziridine, by stirring in MeCN at room temperature. The ring strain in the three‐membered ring could be released through the cleavage of either C−N bond, but ring opening with various nucleophiles proceeded in a highly regio‐ and stereoselective manner. Two possible pathways, in which the aziridine ring was opened by nucleophilic attack at the bridge and the bridgehead, yielded piperidine and azepane rings, respectively. This selective transformation starting from chiral aziridines constitutes an efficient route for the asymmetric synthesis of biologically important natural products, such as fagomines, febrifugine, sedamine, hydroxypipecolic acid, and balanol. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Preparation of a Stable Bicyclic Aziridinium Ion and Its Ring Expansion toward Piperidines and Azepanes

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References (115)

Publisher
Wiley
Copyright
© 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201700080
Publisher site
See Article on Publisher Site

Abstract

The formation of the stable form of 1‐azabicyclo[4.1.0]heptane tosylate was successfully achieved from 2‐[4‐tolenesulfonyloxybutyl]aziridine, by stirring in MeCN at room temperature. The ring strain in the three‐membered ring could be released through the cleavage of either C−N bond, but ring opening with various nucleophiles proceeded in a highly regio‐ and stereoselective manner. Two possible pathways, in which the aziridine ring was opened by nucleophilic attack at the bridge and the bridgehead, yielded piperidine and azepane rings, respectively. This selective transformation starting from chiral aziridines constitutes an efficient route for the asymmetric synthesis of biologically important natural products, such as fagomines, febrifugine, sedamine, hydroxypipecolic acid, and balanol.

Journal

Asian Journal of Organic ChemistryWiley

Published: Sep 1, 2017

Keywords: ; ; ; ;

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