Issue 11, 2011
From the journal:

Chemical Communications

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†

Faïza Diaba*a  and  Josep Bonjoch*a  

* Corresponding authors

a Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain
E-mail: faiza.diaba@ub.edu, josep.bonjoch@ub.edu
Fax: +34 934024539
Tel: +34 934024537

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

DOI
https://doi.org/10.1039/C0CC05105E
Article type
Communication
Submitted
22 Nov 2010
Accepted
12 Jan 2011
First published
28 Jan 2011

Chem. Commun., 2011,47, 3251-3253

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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

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

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