Issue 13, 2003
From the journal:

Organic & Biomolecular Chemistry

An investigation of the Lewis acid mediated 1,3-dipolar cycloaddition between N-benzyl-C-(2-pyridyl)nitrone and allylic alcohol. Direct entry to isoxazolidinyl C-nucleosides†

Pedro Merino,*a   Tomas Tejero,a   Mariano Laguna,b   Elena Cerrada,b   Ana Morenob  and  Jose A. Lopezb  

* Corresponding authors

a Departamento de Quimica Organica Facultad de Ciencias, ICMA, Universidad de Zaragoza, CSIC, Aragon, E-50009 Zaragoza, Spain
E-mail: pmerino@posta.unizar.es
Fax: +34 976 762075
Tel: +34 976 762075

b Departamento de Quimica Inorganica Facultad de Ciencias, ICMA, Universidad de Zaragoza, CSIC, Aragon, E-50009 Zaragoza, Spain

Abstract

The cycloaddition reaction of N-benzyl C-(2-pyridyl) nitrone with allylic alcohol has been carried out to obtain the corresponding 2-benzyl-3-(2-pyridyl)-5-hydroxymethylisoxazolidine. The influence of Lewis acids in the reaction has been studied and a complete 3,5-regioselectivity and cis diastereoselectivity was observed when the reaction was carried out with 1.0 equiv of AgOTf, [Ag(OClO3)(PPh2Me)] or Zn(OTf)2. Insight into the mechanism of the reaction has been obtained by isolating and characterizing (X-ray) the intermediate complexes. Also, a model based on both experimental and theoretical results is proposed.

Graphical abstract: An investigation of the Lewis acid mediated 1,3-dipolar cycloaddition between N-benzyl-C-(2-pyridyl)nitrone and allylic alcohol. Direct entry to isoxazolidinyl C-nucleosides

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Article information

DOI
https://doi.org/10.1039/B304112C
Article type
Paper
Submitted
16 Apr 2003
Accepted
20 May 2003
First published
04 Jun 2003

Org. Biomol. Chem., 2003,1, 2336-2342

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An investigation of the Lewis acid mediated 1,3-dipolar cycloaddition between N-benzyl-C-(2-pyridyl)nitrone and allylic alcohol. Direct entry to isoxazolidinyl C-nucleosides

P. Merino, T. Tejero, M. Laguna, E. Cerrada, A. Moreno and J. A. Lopez, Org. Biomol. Chem., 2003, 1, 2336 DOI: 10.1039/B304112C

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