Issue 29, 2012
From the journal:

RSC Advances

From isoxazolidines to tetrahydro-1,3-oxazines for the synthesis of chiral pyrrolidines†‡

MariFe Flores,a   Pilar García-García,b   Narciso M. Garrido,a   Isidro S. Marcos,a   Francisca Sanzc  and  David Díez*a  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, Salamanca, Spain
E-mail: ddm@usal.es
Fax: +34 923294574
Tel: +34 923294474

b Instituto de Tecnología Química (UPV-CSIC), Universidad Politécnica de Valencia-Consejo Superior de Investigaciones Científicas, Av. De los Naranjos s/n, Valencia, Spain

c Servicio de Difracción de Rayos X, Universidad de Salamanca, Salamanca, Spain
E-mail: sdrayosx@usal.es
Fax: +34 923294574
Tel: +34 923294500

Abstract

A novel approach for the synthesis of chiral tetrasubstituted pyrrolidines has been developed. The rearrangement of isoxazolidines into tetrahydro-1,3-oxazines using reactive organic bromides is herein described for the first time. The subsequent opening reaction of these tetrahydro-1,3-oxazines with nucleophiles probes the usefulness of the method for the synthesis of biologically active compounds.

Graphical abstract: From isoxazolidines to tetrahydro-1,3-oxazines for the synthesis of chiral pyrrolidines

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Article information

DOI
https://doi.org/10.1039/C2RA22110A
Article type
Paper
Submitted
11 Sep 2012
Accepted
12 Sep 2012
First published
17 Sep 2012

RSC Adv., 2012,2, 11040-11048

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From isoxazolidines to tetrahydro-1,3-oxazines for the synthesis of chiral pyrrolidines

M. Flores, P. García-García, N. M. Garrido, I. S. Marcos, F. Sanz and D. Díez, RSC Adv., 2012, 2, 11040 DOI: 10.1039/C2RA22110A

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