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Issue 11, 2011
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NMR evidence of the kinetic and thermodynamic products in the NIS promoted cyclization of 1-phenyl-4-pentenylamines. Synthesis and reactivity of trans-2-phenyl-5-iodopiperidines

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Abstract

The intramolecular reaction of secondary amines with tethered alkenes using NIS was studied, which gave insight into the kinetic vs. thermodynamic control of the iodoaminocyclization and the regioselectivity of the aziridinium ring-opening reactions, and led to functionalized piperidines.

Graphical abstract: NMR evidence of the kinetic and thermodynamic products in the NIS promoted cyclization of 1-phenyl-4-pentenylamines. Synthesis and reactivity of trans-2-phenyl-5-iodopiperidines

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Article information


Submitted
22 Nov 2010
Accepted
12 Jan 2011
First published
28 Jan 2011

Chem. Commun., 2011,47, 3251-3253
Article type
Communication

NMR evidence of the kinetic and thermodynamic products in the NIS promoted cyclization of 1-phenyl-4-pentenylamines. Synthesis and reactivity of trans-2-phenyl-5-iodopiperidines

F. Diaba and J. Bonjoch, Chem. Commun., 2011, 47, 3251 DOI: 10.1039/C0CC05105E

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