Issue 26, 2007
From the journal:

Chemical Communications

Nucleophilic 5-endo-trig cyclizations of N-homoallylic sulfonamides: a facile method for the construction of pyrrolidine rings†

Junji Ichikawa,*a   Guillaume Lapointea  and  Yu Iwaia  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Japan
E-mail: junji@chem.s.u-tokyo.ac.jp
Fax: +81-3-5841-4345
Tel: +81-3-5841-4345

Abstract

Normally disfavored 5-endo-trig cyclizations proceed in N-homoallylsulfonamides bearing a CF3, CCl3, CO2Et or CN group at the C-3 position, via an intramolecular SN2′-type or addition reaction to construct pyrrolidine rings, even though the system allows a more favorable 5-exo-trig pathway.

Graphical abstract: Nucleophilic 5-endo-trig cyclizations of N-homoallylic sulfonamides: a facile method for the construction of pyrrolidine rings

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Article information

DOI
https://doi.org/10.1039/B618251H
Article type
Communication
Submitted
13 Dec 2006
Accepted
06 Feb 2007
First published
11 Apr 2007

Chem. Commun., 2007, 2698-2700

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Nucleophilic 5-endo-trig cyclizations of N-homoallylic sulfonamides: a facile method for the construction of pyrrolidine rings

J. Ichikawa, G. Lapointe and Y. Iwai, Chem. Commun., 2007, 2698 DOI: 10.1039/B618251H

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