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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.
Asian Journal of Organic Chemistry – Wiley
Published: Sep 1, 2017
Keywords: ; ; ; ;
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